#609 - Who is the Greatest All-Time Pop Star? Pop Star Draft
44 min
•May 13, 202618 days agoSummary
Bobby Bones, Eddie, and Brandon Ray conduct an all-time greatest pop stars draft, each selecting five artists across different eras. The hosts debate selections ranging from Elvis and The Beatles to Taylor Swift and Prince, then compare their teams against AI rankings and historical decade-by-decade pop star lists.
Insights
- Pop star legacy is evaluated across multiple dimensions: chart dominance, cultural impact, longevity, and generational relevance—not just commercial success
- Strategic drafting in entertainment requires balancing historical significance with contemporary appeal to maximize voter engagement
- AI ranking of pop culture figures prioritizes catalog depth, chart consistency, and cross-generational influence over recency bias
- Nostalgia and personal experience significantly influence how audiences perceive pop star greatness, making objective ranking inherently subjective
- Band vs. individual artist debate reveals tension between collective cultural impact and individual artist achievement in pop music history
Trends
Generational representation in pop culture rankings—younger audiences favor modern artists while older demographics value classic era pioneersCross-genre influence becoming a key metric for pop star evaluation (e.g., artists who transcended pop into other genres)Resurgence of catalog-based artist evaluation over single-hit or era-specific fame in determining all-time greatnessInternational and global dominance increasingly weighted in pop star rankings (e.g., ABBA, Shakira, Bad Bunny)Female pop star representation and parity discussions emerging in all-time greatest artist conversationsStreaming era reshaping how historical pop star achievements are contextualized and compared to modern metricsDocumentary and media revival effect on perception of legacy artists (Beatles, Elton John, Prince)Career longevity and reinvention valued more heavily than peak-era dominance in contemporary rankings
Topics
All-Time Greatest Pop Stars RankingPop Music History by Decade (1950s-2020s)Artist Draft Strategy and Selection CriteriaCultural Impact vs. Chart PerformanceBand vs. Solo Artist ComparisonGenerational Pop Star PreferencesInternational Pop Star DominanceCareer Longevity and ReinventionAI-Based Entertainment Ranking SystemsFemale Pop Star RepresentationStreaming Era Impact on Legacy ArtistsDocumentary Effect on Artist PerceptionPop Music Genre EvolutionNostalgia and Personal Experience in RankingsCatalog Depth as Success Metric
Companies
iHeart Media
Podcast network that produces and distributes The BobbyCast show
People
Bobby Bones
Main host of The BobbyCast conducting the all-time pop star draft and sharing personal anecdotes about Lady Gaga and ...
Eddie
Co-host participating in pop star draft, selected Elvis Presley, Madonna, Beyonce, Paul McCartney, and Rihanna
Brandon Ray
Co-host participating in pop star draft, selected Michael Jackson, Britney Spears, Miley Cyrus, Justin Timberlake, an...
Lady Gaga
Bobby shared story of booking her for $10,000 seven months before she became a major star, illustrating rapid career ...
Elton John
Bobby recounted meeting Elton John at a charity event where he performed and kissed Bobby on the mouth while showing ...
Scott Stapp
Eddie mentioned playing ping pong with Scott Stapp backstage before a Creed show
Quotes
"Elvis Presley is the greatest pop star of all time"
Eddie•Early in draft
"I'm going to pander a bit. I'm going to go Taylor Swift"
Bobby Bones•First round pick
"By the time she got there, which was like a seven month period, she exploded. People were lined up outside just to have a shot to hopefully get in"
Bobby Bones•Lady Gaga anecdote
"It's in the mind of the beholder. In the voter. However they want to see it"
Bobby Bones•Discussing Paul McCartney vs Beatles debate
"Your team wins. Modern dominance, historic dominance with the Beatles. Once in a generation artistry with Prince. Chart monsters. There are basically no holes here"
AI Ranking•Final AI evaluation of Bobby's team
Full Transcript
This is an iHeart podcast. Guaranteed human. Hey, it's Bobby Bones. Welcome to episode 609 of the Bobbycast. On this episode, myself, Eddie, Brandon Ray, are going to draft the all time greatest pop stars. Each of us will draft five of the greatest pop stars. And if you're listening to this, you can go vote for who has the best team. Just go to the Bobbycast Instagram. The poll will be up there. So let's get right to it. All time pop star draft. We have a wheel. Let's see who goes first. Spin the wheel, please. Come on, baby. Big money, big money. Come on, baby. No whammies. I need this stupid. Let's go. All right. Eddie is first. Who are you taking as your first overall pop star of all time? Wow. Number one is a lot of pressure. But I'm going to go with the greatest pop star of all time. And that's Elvis Presley. Wow. I did not think after you said the greatest pop star of all time that Elvis Presley would be the answer. I do get why you pick Elvis. I know who you're thinking of. Yeah. And it was between maybe them two. OK. I don't know that I'm going to pick them. But Elvis Presley is number one. Elvis Presley off the board. All right. So Facebook's going to have to really vote for you then. Yeah. That's old. Oh, that's old. All the older people. That's not a TikTok vote. Forget it. But yeah, you get the TikTok Instagram vote. Brandon, you're number two. Oh, it's me now. Yeah. It's not. It goes like a clock. Oh, I'm sorry. Yeah. I thought we were spinning. No, you just go one to thought you were going to say the king of pop, Michael Jackson. Correct. Is that what you're saying? Yeah. That's what I'm saying. OK. Are you disappointed with those two picks? Did we ruin your strategy? No. No. OK. It just depends what you're aiming for. It is all time, but I think I'm going to pander a bit. I'm going to go Taylor Swift. All right. Oh, that's good. This is good. That's really good. I thought Taylor would make it to the second round, but I like it. These were pretty good errors. Like you had old school, old school. I had like our childhood and now you have current. Yeah. I mean, that checks. Yeah. You know. Older. Are you? What are you even talking about? Wait, who's older? I'm older than Brandon. Oh, you are? Yeah. OK. So you are pandering. I'm pandering. I think right now. That's very smart. I'm going to vote for Taylor Swift. Very smart. Yeah. But I'm going Taylor Swift is my number one post-door of all time. OK. All right. Back over to you, Eddie. Your round two pick. OK. I feel like she was huge. Never was a fan of hers, really. A lot of controversy around her. Even, you know, the last 10 years, I would say she was still controversial. So I'm going to go Madonna. That's my second one. Man, you really did not think you were going to say. But wow, man. Madonna. OK. So Elvis and Madonna. Yeah. Got it. Madonna's a good one. I should get it easily been picked in the first round as well. Right. Did not think by your setup. That's what you were saying. I wonder what you guys were thinking. Well, I'm going to give the same setup. A lot of controversy. A lot of a lot of hit songs. Guys, hit me, baby, one more time. I'm going to go with Britney Spears. I was going to go Britney next. My next pick was going to be Britney if it was. OK. Dang. Didn't make my list, guys. Wow. OK, it's over to me. It's tough just getting the third overall pick, by the way. I'd like everybody to know. I got it. It really is. Yeah. So I would have picked Britney Spears with this pick. I want to go with someone who has been a massive pop star for a couple of decades. And there are. Different versions of how popular this star is. And I think now more popular than ever, even though when this person became a pop star. Was a massive force. And I guess now more popular than ever. So I'm going to go with the current person again. Now more popular. Oh. Oh, right. It down. Oh, well, because if I if I don't, if that's not who it is, I'm going to. Right, right. I don't feel like I want to guess to give somebody. I really don't want to guess it. OK, actually, my second pick then will be. Because I'm a believer, Justin Bieber. Oh, that's good. OK, OK. I didn't think you were going to go that way. But I'm very good. We said about both my picks. Yes, I know. Dude, that's it. That's a list. And I'm going to. And the reason when Bieber was a kid. Like the first YouTube massive star, the first kid that launched from YouTube, massive star, but my wife, who's in her 30s, watched both full sets of him at Coachella. We watched on screen. Yeah, like people are as passionate now. And like he has a real credibility as an artist. He's grown from just being, you know, pop, putting out easy to make pop songs written by other people and producers to now he's like a real life dude. Yeah, for sure. So I'm going Justin Bieber as my number two pick on the pop star team. Wow. What a list. Elvis Madonna. All right, you have Elvis and Madonna. Anybody else dead you like to put on there? Yeah, Madonna is not dead. Oh, why did you just kill her? So it's not not dead in the physical sense. Yeah, yeah, yeah. Yeah, she did do Coachella with Sprinty Carpenter. There you go. Thank you guys. So I think that I'm going to pander a little bit here, too. I believe that if I put her on my list, I think I will definitely get some good votes out there. Give me Queen B Beyonce. OK. That's a good one. Thank you. I probably take it on a different round, but you know what? Really? For you. Have at it. I think she fits perfect on my team. Elvis Madonna, Beyonce. Very diverse. Yeah, that's true. Especially in decades. Yeah, exactly. All right. Brandon, you have Michael Jackson and Britney Spears. I feel like this person will pander. She definitely will. We're all the same. Pander every pick now. But she is more relevant now than ever again. I came in like a wrecking ball with Miley Cyrus. Oh, that's a good one. I didn't have her on my list and that is a good one. I that's who I added late thinking that you were going to pick Miley. Do you like the catch phrases? Like when I say the song before or should I just say the name? You do you, man. OK, yeah, you do you. Except everybody stops saying pander. I use it once and all of a sudden you guys learned a new word. I mean, I just want to do it three times. That's not good. He was third. All right. For my third pick out of five, let's see. I have Taylor Swift and Justin Bieber. So. Don't use it. Don't do it. You were. I'm torn between two. Well, what are the two? No, because you'll take one. Exactly. And one of them I don't know is popped up on you guys list. But one of them is also the P word. Oh, I have a P word. I do have a word. Yep. It's not pander. Neither is I'm going to go with if we're doing greatest pop stars. Of all time, I'm going to go with the Beatles. Wait, does that count as a pop star? Absolutely. Prandon popular star pop radio. Aren't they four stars? The Beatles is an entity. I feel like the Beatles are. Oh, fine. I got you. Fine. If you want to play that game, I got you. It's not a game. I got you. Do you guys not feel like the Beatles? We can vote. No, you could do it, dude. Go for it. No, I think. Yeah, I feel like nothing to me screamed pop like them playing Ed Sullivan and watching all those teenage girls scream their faces off. That to me was Justin Bieber and black and white. They were definitely a pop band. I just didn't know we were going to put a band in there. But you didn't ask. No, I don't know. There were no rules. No rules. Go for it. I like it. The Beatles. But there's nobody that's going to be a bigger band that you're going to take. So you're like, oh, OK, well, now I'm going to break the rules. That's the biggest. You're right. That's the biggest pop band that we know. For sure. That's still just as relevant today. You got Beyonce covering Beatles songs. You've got all the documentaries coming out. I mean, it's still. Man, why am I helping you? I'm thinking about my next pick and I feel like I'm doing this out of spite. And I shouldn't. I should. County Crows. I know what you're going to say. I write it down. Just like go with whatever I was going to do. The monkeys. No, no. OK, so. Know what you're going to say. You have. But not as quiet. I mean, so you have Elvis Madonna and Beyonce at number four on your list is going to be here. I'm going to go with the pop star and inspired by your last pick. Paul McCartney. I got a. That's not going to Paul McCartney. I got a. That's not going to Paul McCartney. I got a. That's not going to Paul McCartney. I got a. I agree. The Paul McCartney is one part of the Beatles. Right. Ebony. No. And. Well, then put Stevie Wonder on there. Well, no, that's just to do what they did. I have Stevie Wonder on my list, but. That's that's. I feel like that strategically was a bad move by you. And that's what I meant by like I'm picking this by out of spite and I shouldn't have. But you know what? Pick Ringo Brandon really spite me. Yeah, do it. Do it. Do it. Brandon, to add to your team, Michael Jackson, Britney Spears and Miley Cyrus. Oh man, I am torn and not Natalie. Natalie and Brulia. That's not on my list. I'm going to say. Justin Timberlake. I had him on my list. Dang. I'm surprised that you went Timberlake over in sync. Well, I'm thinking now as well. I'm thinking career span, right? What's in sync doing today? Nothing. Waiting for Justin Timberlake to let them do a reunion tour. Yeah, please. I hear you, but I don't think, in my opinion, a massive pop career is really defined by how long you can do it. Well, that's not what I mean. What do you mean? You just said to rate. Then you said, well, you said span career span. Well, with Justin Timberlake, you get in sync. No, you don't. As well. You don't get in sync as well. And to see that's my theory too with Paul McCartney. You get the Beatles. With Timberlake, you get from like I love you on, because I think that was his first song. What about Mickey Mouse Club? Okay, you can have pre-start search. It changes everything. I see what you mean. You don't get in sync. But there are no rules. But there are no rules. No, the rules are you have to pick them, but you don't get the Beatles. But it's in the mind. It's in the mind of the beholder. Correct. In the voter. In the voter. However they want to see it. But they're not going to see. They're just going to see Justin Timberlake. And they're going to be like, oh my God, I love him in in sync. We'll put this up on the Bobby Cast Instagram. We'll vote on the poll there. We'll put everybody, we'll put like a picture of all of these. Love it. And they can vote one, two or three. But I don't think Justin Timberlake or Paul McCartney by themselves evoke as much emotion as in sync or the Beatles. Sure, in your mind. But the voter could see it. It's all in the heart of the beholder. But you're not getting J.C. Shazae when you put Justin Timberlake. You're not getting L.A. You're not getting Paton. You're not getting Chris Kirkpatrick. You're not getting Joey Fatone. Right. Yes. Which I had Joey Fatone. Oh yeah. Take that. I'll take him out. I just picked members of all y'all's bands. Okay. Number four for me with Taylor Bieber and the Beatles. The question is you all know about the P word. Oh, so Paul McCartney wasn't your P word. No. Okay. You think I was going to pick the Beatles and then Paul McCartney? I mean, double down. Oh, no, double down. I didn't think Paul McCartney. What? I know who your P word is. I know who he's going to say to. I thought you would have thought that originally. But then I thought of Paul McCartney. Another P word. Okay. I'm running out of pop stars, guys. Well, I have a million, but I just there's like tears. I'm going Mariah Carey. Oh, bro, you're so good. That's solid. I have it. Because I think she's a solid top 10. That was. But I don't think she's anybody's top three or four. I think where we are now at number four on the list. Mariah Carey is my four. Okay. Oh, we all have one left. You want a P word? Should I take the word? Let me look at my. Okay. 1950s Elvis in the 50s. Madonna's 60s Elvis. Yeah. 60s 50s, 60s. Got it. Madonna 80s. Beyonce. And I 2000s. Because you didn't pick Destiny's Child. Right. Just be. Oh, should I do that? Okay. Paul McCartney, you got 1960s all the way. You don't have Beatles. You don't get Beatles with Paul McCartney. You get Paul McCartney. You know what? Heck, you can have wings. Wings jam. You can have Paul McCartney and wings. Wings is awesome with his wife. Linda. Fallen Linda. Okay. Gosh, what do we do here? This is my last pick. Do I go modern or do I go with a legend? You really don't have. Beyonce is pretty modern. She's the only modern. Yeah, you really don't have anybody super modern. Right. But it is all time. It is all time. And I feel like we can't go too modern because, you know, there's just like like like Brandon was saying that career span isn't a lot for them to be like a huge pop star. But. I'm between two P word. E word and R word. P word. I know that one. E word. Ooh. Two, two, two names on E word. Two is one name. Word. And R word is one name. Yes, you got my word. Yeah. I think you got my place on my list. Place on my list. Place on my list. Place on my list. All right. All right. I made my decision. I'm going with our word. Rihanna. Oh, that's your say Ringo. Okay, Rihanna. That is a very good. Broad choice of pop pop pop pop stars. Of pop stars. Like it's pretty broad. I like it. I think this feels like at the end of a fantasy football draft where you feel like your team is the best just because you drafted them and you were close to that. And everybody else is like, I mean, it's fine. That's him every year. Yeah, but you're like, no, man, this is it. Yeah, I'm convinced of myself. This is pretty good. Let's take a quick pause for a message from our sponsor. And we're back on the Bobby cast. All right, Brandon, your fifth and final pick. Okay. Michael Jackson, Britney Spears, Miley Cyrus, Justin Timberlake. Who will you put on your pop star draft? This is tough. Um, I'm between three as well. Give us the words. I've got a B. Mm hmm. I've got an L. And I've got a W. Why? Okay, I know all three of them. Not why Nona, bro. Why Nona, Judd? I think yours are going to be. What's the W? B is probably going to be Bruno Mars. I don't know. The L is probably going to be Lady Gaga. Oh, yeah. And what was the other one? W. W part, the weekend. Wayland Jennings. My number five. Pick the weekend and pick Wayland Jennings. Pick Wayland. Oh man. My number five is Whitney Houston. Oh, that's the W. That's the W. That's better than weekend. It's way better than weekend. Yeah. Good job, dude. Did you guys think W was Whitney Houston? What'd you think weekend? You didn't know? That weekend? Yeah. Yeah. Wow. I will always love you. All right, good team. That's a solid team, Brandon. Lady Gaga solid though, too. If you'd have picked Lady Gaga, I'd have picked you. Lady Gaga, yeah. Once, way back in my early radio days, Lady Gaga had just put out her first song. It wasn't a hit yet. And we paid her $10,000 to come do a show for us. The morning show, my morning show. $10,000 total. And she came and was the artist at something we had called Second Chance Prom, just so adults could get back together. And we had an artist that would play, but usually it was somebody small, but she was so, so, so new. In the time that we paid the $10,000 till the time that she got there, which was like a seven month period, she exploded. That's insane. People were lined up outside and you had to buy tickets ahead of time. People were lined up outside just to have a shot to hopefully get in. It was really one of the most lightning in a bottle things that's ever happened to me in my career. Because again, there was really no foresight and I bet she's going to blow up because I'm probably using the who knows who's going to blow up. But we played Lady Gaga, $10,000. And by the time to book her, then we looked, it was like $250,000 to get her to come do anything because she had two hits, but she, you know, super pop. But yeah, I don't pick her, but that show was awesome. Eddie, you were there. I was there. And I remember the line. I remember pulling up and being like, wow, everyone is trying to get in here because she had blown up. As a small couple thousand. Yeah. And were you working for the news then? I was. Eddie wasn't working with me. He was like a news reporter. And I'd asked you for a couple tickets. You hooked me up a couple tickets. Like Austin, $10,000. How did that moment stack up? Lady Gaga, how would you compare Lady Gaga to playing ping pong with Scott Stapp? Creed. Well, playing ping pong with Scott Stapp backstage before a Creed show was free. Oh, yeah, it's true. But he whooped me. Really? Like he was really good. He was really, really, you know, with arms. Okay. So I got one more pick here. So now I can talk mine out. So P is Prince, obviously. Obviously. Obviously. Well, I have another P. Who else would you have pink? Oh, pink's good too. She didn't make the Rockin' On Hall of Fame this year, did she? No. We know we were right. We voted for her, right? No, we didn't only because we felt like she was too relevant. And there were certain people, if they didn't make it this year, that we felt like they would die. Yeah. So we put some of them in. So Prince is on my list. Lady Gaga's on my list. Bruno Mars is on my list. Katy Perry's on my list, but not a great person. So I'm going to stay away from her. I don't think you'd draft her. No, thanks. Also have Usher. I've had Sheeran. That's a good one. I have, I'm not going to pick it, but when I went all the way through, I did pick a global dominance. Jason Derulo. Why would that come to mind? I don't know. Global? Jason Derulo. Why does that mean global? He's huge, right? Anybody? Derulo's pretty big. Yeah, but he's a global dominance. I was thinking Abba. Oh, wow. But I don't look at the day. But I don't. And you picked the Elvis, dude. I thought you were going to say. I know. I thought you were going to say you too. Oh, yeah. So let's not give him anymore. Well, it's over. No, it's not over. He's got a pick. I still got to pick one. Okay. Because you choose a good one. But Abba, I don't think people understand just how big, unless you like know, or you're from Europe, or you look, I don't think you know how big Abba really was. Right. Yeah, yeah. Because all over the world, they were monsters. I have one that is super legend pick. And I don't really have an era. I have the Beatles. I don't know if I want to go double era. Are you another band? I think another band. Okay. You're done with bands. Yeah. Where did they, where they and we are the world? Oh, good question. No, I think Stevie Wonder's a fun one to Ray Charles. Well, hey, what are you doing? Got to stop giving me. I wouldn't pick Ray Charles over Stevie Wonder though. So once I said Stevie Wonder, Ray Charles was off. Um, yeah, only I'm vision impaired. So I can only have one other vision impaired person. We don't want a whole. Too much. Another one that I thought about. And again, I think it was, it was like older pop, was Celine Dion. That's a good one. Yeah, I thought about her. She was doing her thing. And then I thought Shakira International. Yeah. For 25, 30 years. Yeah. Yeah. And then I thought David Bowie. Oh, David Bowie's a good one. Yeah. Wow. I have a lot of options here for that last pick. Well, I also thought somebody that I'm friends with, Lionel Richie. Yeah, that's a great one. We are the world. The ringleader, man. And then he was the ringleader. When I picked the Beatles, it kind of killed me from taking the Spice Girls. Because I was only going to put one band. Because the Spice Girls. That was my six. Spice Girls. Yeah. You should still do the Spice Girls. I think you should. Please do the Sklubble Dominance. I think I'm going to go. Spice. Spice of your life. I just, I have a pick that I feel like it's so good for me to pick, but I don't think people are going to get it. What do you mean? They're not going to get it? Kind of crows? Mm-mm. I don't think they're going to understand how big of a pop star I was because I'm only going to remember him from a different phase in his life. Interesting. Oh. I wonder if I'm thinking of the same person. No. Who is that? John Mayer. No. Just start with a G. Mm-mm. Who's that? George Michael. No, but I did have him way down my list. Wham. You have Garth in there? Mm-mm. Not a pop star. Ooh. Crossed over a little bit. Not a pop star. I'm sure. I'm sure. What are you thinking of? Somebody that thought was fun was Phil Collins, though. That's a good one. 80s for sure. But even when he was at his most pop, he was still dressing like a banker. Yes. Polos. Kakis with a button on. Skinny tie. Lofors. OK, I'll tell you who I'm bouncing between. And I don't need any reaction. Fine. Because I've eliminated all the boy bands. Backstreet Boys were definitely going to be up there. But I feel like if I'm doing the Beatles, I got to cut the bands out of the rest of it. Yeah, because that was cheap anyway. Yeah. So that was one. Jennifer Lopez. I thought a J. Loeb one. Yeah. It was a good one. Is she still who you're trying to say? But the one that I'm really leaning toward is Frank Sinatra. That's a good one. Because nobody in that he's like the king. But let me tell you, man, back in the day. That's on that. He was. But I think so many people will just know him from being old. Yeah. I mean, I'm not going to help you. But man, he was the pop star back in the day. I'm going to go with Prince. The P-word. I'm going to have to go to the P-word. He's just relevant enough. That's good. Most people's lives who are probably watching or listening to this. I just felt like Frank Sinatra was a little too old. It's kind of like the Willie Nelson syndrome. We only remember Willie old. Even pictures. Willie's always been old. Even when he wasn't. Yeah. So OK. And he's got Elvis Madonna, Beyonce, Paul McCartney. I think that's your weakest because you just took something out of a bag. No, he covers the whole Beatles. But yeah. And I think had he been ahead of the pick of the Beatles out of the matter. I was just thinking that. Because he's at four and the Beatles are three. It definitely looks like he read me on. I was just thinking that. And Rihanna is at five on Eddie's team. Rihanna. Brandon Michael Jackson, Britney Spears, Miley Cyrus, Justin Timberlake, Whitney Houston. Brandon, that is solid. Solid. Taylor Swift, Justin Bieber, The Beatles, Mariah Carey Prince. Oh, that's solid. I mean, all the every list is really solid. Mike, who's the weakest of all those? You want to see what AI said is the weakest? Here we go. I don't always trust AI, though. Yeah, but let's see what they say. What does AI? Because AI. I put them all in and it ranked everybody. AI can't give Paul McCartney the win, though. I'm afraid. I kind of agree with it. You agree with the ranking. AI? OK. Are you scared of the Paul McCartney fight? I'll put it up there if you want me to. OK, let's see what AI says. Go ahead. I know what I believe in it. Oh, wow. You know what I believe in it. I thought Bobby would win. In third place, Brandon. This is, according to the AI, still a killer lineup, but slightly less balanced. Everybody listening, don't just pause it. Just mute it real quick. Michael Jackson, the greatest pop star ever. Britney Spears, pop princess, Miley Cyrus, versatile. But less. Justin Timberlake, strong but not top tier, Whitney Houston, one of the greatest voices ever. Why Brandon's at three? Having Michael Jackson and Whitney Houston is insane, but after that, it dips slightly. Wow. Less total catalog dominance and fewer undisputed goat tier. Oh, goat tier. Across the roster. OK. Eddie. Elvis Medonna, Beyonce, Paul McCartney, Rihanna. This team screams icon status and longevity. You nailed it, AI. Elvis, the original pop superstar. Medonna, the blueprint. Beyonce, elite performer and cultural force. Paul McCartney, Beatles legacy. Yes. Thank you, AI. Rihanna hit machine. While this might be the coolest team, it spans generations perfectly. It's loaded with icons. They lose a little edge to Bobby's team and peak chart dominance and overall depth of hits across all members. Oh, the stats. Interesting. So if we go to mine, they call mine the Avengers of pop. Wow. That's pretty good. Taylor Swift, arguably the most dominant artist of the modern era. Justin Bieber, massive global pop force for 15 plus years. The Beatles, the most influential band of pop history. Mariah Carey, one of the best selling artists ever. And Prince, elite talent, innovation, and cultural impact. Why this team wins. Modern dominance, historic dominance with the Beatles. Once in a generation, artistry with Prince, chart monsters. There are basically no holes here. Every category is covered at an elite level. Good job. I guess I want to know what that then. No. No, we will let the people vote. No, we will let the people vote. I guess it's fine. I did not think that I would win if asked by AI. I thought that Brandon would be the winner. I think, I mean, AI is thinking about it in a different way. Like, if you look at it that way, absolutely. Mike, what's the question you asked it? I just put the prompt up here. So we can see exactly what Mike asked. I said, can you rank each of these pop stars on who has the best and strongest team, this list? Oh, I mean, that's what people are going to do. I think that's good. It is subjective. So AI gets what, one vote? Sure. Is it electoral college? Yeah. All right. Exactly. What about honorable mentions? Can we explore? Yeah, I mean, I feel like I actually listed off like putting it on my list. Everything that you were listing. Except you didn't have Elton John. I thought you picked him. I didn't. He was one of the ones that was debating. I think because you mentioned him, I didn't mention him again. I thought you were going to say Cold Play after Bobby brought up bands. Oh, interesting. No, when I was thinking about a possible band, it'd be the Rolling Stones. I thought about leading with a boy band, but then I thought, one of you guys would grab the Beatles if I did that. So I knew if I came with the Beatles first, there really was nothing else you could come with. Aretha Franklin was on my list. That's a good one. That's good. But again, these are just historical people that I only know of from watching documentaries and listening to old music. I didn't get to experience that pop thing. And for me, the Beatles thing is the same, but that Ed Sullivan performance. I can think of the Beatles doing Ed Sullivan, playing in Shea Stadium, the Mets. I've seen that a thousand times. All the girls in the crowd crying. Yeah. OK, biggest pop star of the 50s. Elvis. Yeah. Let's see. Probably Elvis, right? Yeah. But so Frank Sinatra, so he was 50s, right? So that would have been up against Elvis. The biggest pop star of the 50s, Elvis Presley. You're right there. I think of his at his Ed Sullivan show too. Oh, yeah. Frank Sinatra at two, Chuck Berry at three. Oh, wow. Little Richard at four, and then one of my favorites of all time at five. Every day. Oh, yeah, buddy, buddy, manly. Yes, that's good. Very short run. Yeah. OK, let's go to the 60s. Can you guess who they're going to say is the biggest pop star of the 60s? The 60s. The Beatles. Oh, it still could be the Beatles. OK, let's take anybody out we've asked. I was going to have somebody knew. OK. Because Beatles are number one. They are? Yeah, they are number one. They were also the 50s. But who do you think it would be? Somebody that we haven't listed. Or someone that hasn't. There wasn't the winner of the 50s. I see this one. I'm going to play the next round, because I haven't looked up the next round. OK. The 60s. It's, I guess, every all music back then was pop, right? Like they didn't really separate genres. Yeah, unless it was like country and Western. Yeah. Like I mean, it was all pop, because yes, I agree. Like Beach Boys. Oh, what a great, the Beach Boys. I've never thought about the Beach Boys. Yeah. I've been a good one. Bob Dylan. Man. The 60s. 60s. This is. When I tell you, yeah, it makes sense. Hmm. What's the name start with? I would say it was, if you weren't, what's the name start with? Yeah. Is it a band? Yeah. It's a band. OK. It's a band, and I would think most people fought. Just like Kendrick Lamar, I would think it was either the Beatles or Beach Boys. No. Oh, Rolling Stones. The Rolling Stones. Oh, wow. So they do have the Beatles at number one. But they have the Rolling Stones at number two. Elvis at three, but he was the 50s guy. Aretha at four, and the Supremes at five. Wow. That's, yeah. I have not looked at the 70s yet. So who would we say? OK. On my list, I almost picked it after you said the Beatles. But I'm just thinking of cultural and chart dominance. Led Zeppelin. The Bee Gees. The Bee Gees is a good one of the 70s. The Bee Gees would be my abapick. OK. Yeah. Where I, massive, but I don't think the significance of the Bee Gees is really known by like people in America, even though they were big here. I mean, I'm thinking about this list. The AI, what it would say. The Bee Gees is a great pick. I don't think I would ever got there. They, I think Barry Gebrough, I'm in the stream. Yeah. And produced it. Wow. So dolly, you know that. Yeah. You. OK. So I'm going to go. I still think David Bowie is big. So he's 70s for that thing. Yeah. David Bowie. What about like Stevie Wonder? That's 70s, right? Yeah. Oh, it's good. Because he lived in a few generations. Because I saw him on the Cosby Show in the 80s, and that's when I became. Because there was like the accident where they rear-ended Stevie Wonder. And so the Cosby Show, they go to his studio, the recording studio, and they're like, oh, it's Stevie Wonder. And he's like in the studio, I'm just going to record a little something. And I don't remember this exactly. But then he's like playing his I just call to sail. And then they have everybody up singing along with the song. That's right. No, dude. It's crazy because those episodes don't live long now because we can't watch the Cosby Show anymore. Right. So. You just said one. You thought I was going to say Led Zeppelin. That's a. Zeppelin. That's a good one. David Bowie. Billy Joel. Yes. That's a really interesting. I would have put him in the 80s for me. That feels early, early Billy Joel. Yeah. Because like piano, man, I think that's 70s. I'd be wrong about that. I would have guessed 80s. OK, I haven't hit this yet. So I don't know who it is. I'm going to. It's got to be somebody we've mentioned. And I would even still keep Abba in there. Is there anybody we're forgetting from the 70s? I got one. Is there anybody from Woodstock? That was 69, but that does it. Rolls over. I got a good one. Go ahead. If you were talking about 70s, Barbara Streisand. Oh, I know nothing about her. That's so good, though. Yes. If I mean, not me personally, but I'm just saying. It's OK. It's OK. If you were a big fan. Yeah. OK, are we ready? Thank you. It's Barbara. Come on. In the 70s, it was. Oh, we missed it. Did we miss it? We missed it. We missed it. We're so stupid. Hold on. And you know what? All of ours ended up making the list because at number two was Abba. At number three was Stevie Wonder. At number four with the Bee Gees. Great, great pick there. Number five was David Bowie. We missed it. No way. I'll read you a little. Oh, Elton John. Yes. Elton John. Huge. So stupid. Huge. Did you feel that? Elton John hit machine. Your song, Rock It Man, Crockett Out Rock, Been In The Jets, Don't Go Breaking My Heart. Multiple albums a year at times back then. Crazy. Huge in the US and internationally. His outfits, his longevity. Also, the only dude I've ever kissed on the mouth. The only one? Wow. The Bobby Cast will be right back. This is The Bobby Cast. I'm almost certain the only dude I've ever kissed on the mouth. Yeah, when did that happen again? A charity event. And we were sit, we were, he was that main performer. I was hosting it and telling jokes. So we're sitting together. It was right whenever him and his husband had adopted a child and he had his iPad out. And he was showing us pictures of his baby. He was so happy. And we had dinner and there's like eight of us sitting around this table. It wasn't a big room. And so the whole time it was pretty crazy. I'm sitting next to Elton John having dinner. And so I go up and do my thing and tell a few jokes and do some of the lifting. Like this is how you donate. And you had to pay a decent amount to get into this place to watch. It's a private Elton John show. And so I didn't because I was hosting it for the record high. I shouldn't say that. I should be like, yeah, I also paid for the chair. Yeah, you go off and donate it for the record. So everyone knows. I'm so stupid. And how much did you donate? And so he goes up and it's just him on a piano. And he has so many songs. He has a prompter of all his lyrics. And so he's playing them all. And at the end of every song, he would stand up and get a standing ovation. It was like built in. Wow. So he'd get a standing ovation every song. He'd sit back down and play another one. And at the very, very end, he would go down and he was like shaking everybody's hand and he grabs me and he goes, plant a big one on me and just keeps walking. Nice. That's so cool. Yeah, it's really cool. What a great memory. It is really cool. Yeah. Help me, John. Wow. Okay. I think the 80s is easily going to be Michael Jackson. Like that's so easy. It has to be Michael Jackson. Who's going to be number two? Madonna. Oh, Madonna. Madonna is huge. Yeah. Madonna's got to be two. After you mentioned bands, I mean, in the 80s, I think of like, that's a good one. Oh, wow. I think of like Cindy Lauper. Oh, that's a good one. Cindy Lauper. But then, you know, we could talk about like 80s hair bands, but like the cultural impact, kiss. Kiss and have they like one couple of songs couple songs. What are they just face paint? Sure. You sure? Yeah. Well, what about like Ozzy? I bet you're five. Ozzy's good. I think Ozzy's 60s, 70s though. 70s. Okay. Because you think like Black Sabbath. Because Ozzy would be like 80s. I think there's no change. I think if I said give me top 50 of the 80s, kiss wouldn't be on the list. Top 50 pop. Yeah. Yeah. You think there would be cultural significance. I think that makes you pop. I think there would be in the top 25. I think they would. Top 50 maybe wrong. Top 25. Okay. Let's go to 80s. Okay. What do you think it's going to be? Michael Jackson. Madonna. Madonna. So if I can pull the whole top five here. Okay. Okay. Prints. Yes. Prints. Okay. When was early 80s? Early 80s. Yeah. I'm thinking of Lionel Richie. Lionel Richie too. Okay. Let's see. Guys, where was Queen in the 70s? 70s. Okay. So much to say. All right. Here we go. From the 80s, top five. Michael Jackson at number one. Okay. Obviously. Number two. Madonna. Okay. Number three. Kiss. Prints. Jesus. So we got all, we have four of the five. Okay. Number five was George Michael. Okay. So it wasn't there. Okay. Good. Number four was Whitney Houston. Oh, my God. So it was MJ, Madonna, Prints, Whitney Houston and George Michael. Okay. 90s. It's got to be boy bands, right? Britney Spears. It's got to be number one. Yes. Britney Spears, boy bands, Christina Aguilera. Okay. So the boy bands will be. Battery Boys and N.C. Those will be the two. Okay. I say it's Britney. At one. Why? Who do you think that would open? That's, is it, how, how late 90s was, was Britney and like N.C. That was that like 96, 97. No, it was later than that. Okay. There you go. Something like, if you say Nirvana. Yeah. I'm thinking like Kurt Cobain, like the grunge. I still say Britney. Oh, for sure. But I'm thinking for the other ones, like, I mean, you could even say Cheryl Crowe. What about like MC Hammer? Oh, that's one in Wonderland allies. Hammer had a little more. Okay. What we're predicting what they're going to say. My prediction is going to be Britney. Oh, you're right about 2000s though. Okay. That's boy bands. Yeah. It's going to be Britney, a couple boy bands, Nirvana. Okay. With the early 90s. And Tupac. Oh, I forgot about the rappers. Oh yeah. I'm going to add one for 90s. Celine Dion. Yeah. That's a good one. Celine Dion always felt like old person pop. For sure. She did. Yes. Yes. She did. Like, you know, the mixed station, the 80s, 90s of today. Easy list. Like it was like the three songs from today that they would play in their 80s, 90s and today with Celine Dion. So who's our number one in the 90s? I think you, I don't have an answer here. I think it's going to be Britney. I do too. But I, it's so late. I remember 98, 99 playing that baby one more time for the first time. I was in radio as a teenager. It, I mean, Christina Aguilera is massive too. But again, that's going to be 2000s. Yeah. You want 90s? You want it? Hit it. Top five. The number one is... Voice to Man. Can't be because it's Madonna. Oh, okay. And although she came back and had Ray Alight, which was a jam. I don't, I don't feel like it's Madonna. I don't know. No, no, no, no. I'm like 90, 91, 92. And that does count. But man, she did hit hard again. Remember the song, music, when it came out? Oh yeah. That was awesome. In the music. I don't know what you're doing. In the... How did that song go? Music. Dance to the random. Yeah, that's it. That's it. Yeah. Ray Alight. Okay. Here we go. Top five. The, so this is, there's only Michael Jackson's on the list. So that had to be early 90s. He was. Whitney Houston's on the list. So that was the 90s bodyguard. I'm going to ask for some extras here because our list, we couldn't have repeats. Mariah Carey. Yes. So. Janet Jackson. Madonna. Michael Jackson and Whitney Houston were the top three. We're going to knock them off. Okay. Their list here, Mariah Carey, number one hit machine of the decade. Makes sense all through the 90s. For sure. Number two, Celine Dion. Oh, here we go. Number three, Britney Spears, Backstreet Boys, because they were a little before in sync and Spice Girls. Very cool. Spice Girls. Yeah. Spice Girls have other songs other than, uh, want to be, to become one. Oh. To become one. I do remember that one. Oh, dude. Uh, Spice. Spice of your life. So they have, they have, want to be Spice Up Your, or Spice, Spice Up Your Life. Spice of your life. Was that for the movie? Giving you everything, all the joy you can bring. This I swear. There you go. This I swear. That was sporty. She, she brought it. She was actually the talent of the whole band. Oh, was she really? Yes. Best singer, everything. Yeah. Uh, Spice Girls. Top stream songs, want to be, Say You'll Be There. Say You'll Be There. That's that, that was that one, right? Yeah. I bought the, I bought the single on a CD at Hastings in Pampet, Texas. Wow. Uh, To Become One. To Become One. So when you get to take them. To become one. I don't know, Viva Forever. Hmm. But Spice Up Your Life. Uh, okay. Uh, okay. And then let's do. 2000s. 2000s. That's gotta be. Brittany. If we're not, if we're not putting Brittany and Backstreet Boys in there, it's gotta have to be like, it's insane. It's in sync. It's in sync for sure. I'm gonna say 2000s, but no. I feel like this is, Brittany. This is also where the rap comes into. Backstreet or Spice Girls. Big time. Like the, the biggie and the. Yeah. We're going in sync and Will Smith, Fresh Prince. Oh. Now in every 90s, every 90s, every 90s. Is this like Puff, Pete Diddy? Yeah. This was his time. Eddie's like, is it Puff Daddy, R Kelly? I mean, that was the time. That was the time. That was me. That was me. Hmm. Hmm. I'm going in sync. In sync. In 2000s. It's just a weird era because I don't know that. It's Shania. Any, possibly. Okay. Here we go. Pink. Ah, pink's a good one. So, when pink was starting to dominate or was that 2010s? Whoa, whoa, whoa. What do you see? Beyonce. Oh, Beyonce. There you go. Oh, here's a good one. Eminem. Perfect. Usher. Usher. Rihanna. Justin Timberlake. Okay. Add 2010. Now it's like, is it Bieber? Oh gosh, who knows? Nickelback. 2010s. Read. Nickelback. Taylor Swift. It's number one. And then we have Drake, Rihanna, Adele, Kanye. I was thinking about Adele for your pop star. For my, yeah, for my list, but. 2020s. Taylor Swift. Taylor Swift. Ed Sheeran. Oh, that's good. Bad Bunny, The Weeknd, Drake, Olivia Rodrigo. Oh, nice. Post Malone and Honorable Mention. Billie Eilish. So there you go. We did a lot of pop talk there. Yeah, man. That feels good to be the champ. Oh, we're still voting? No, no, you're not the champ. You're not the champ. That was just a guy. According to AI. So just at, is it the Bobby Cast or Bobby Cast? The. Okay. At the Bobby Cast. We will put it up. Go vote and hey, if I lose, I'll still say I was the winner. Let's be honest. There you go. Nice job, everybody. Thanks for listening to a Bobby Cast production. This is an I heart podcast. Guaranteed human.