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Classic Entertainment Rivalries!

Hey, I have an idea! Let's watch people with way more money, way more fame, and way bigger egos than any of us could ever imagine just absolutely go at each other.


I gotta tell you, sometimes I love it. I really do. There’s something endlessly entertaining about rivalries in show business. Always has been.


And part of that is because entertainment, at its core, is built on ego. Let’s be honest. You don’t become a movie star or a rock god or a legendary TV personality without a pretty healthy sense of self…or in some cases, an incredibly unhealthy, gigantic, out-of-control sense of self.


You mix that with fame, money, pressure, attention, awards, critics, fans, social media now…you throw all that into a blender, and what do you get? You get feuds. You get rivalries.


You get people sniping at each other, writing songs about each other, taking shots in interviews, sometimes throwing punches, sometimes filing lawsuits, and occasionally, yeah, sometimes things get really, really ugly.


Now, this stuff has been around forever. This isn’t new. Rivalries in entertainment go back to the beginning of the business. Stage actors in the early days, silent film stars, classic Hollywood legends, musicians in the ‘50s, ‘60s, ‘70s…all the way up to now. It’s baked into the cake.


And it’s only gotten louder and more ridiculous in the age of the internet, where every little comment gets blown up into a headline and suddenly you’ve got a full-blown feud trending on social media because somebody liked the wrong tweet. It’s insane.


And look, I want to be clear about something. I’m not talking about world politics, I’m not talking about wars, I’m not talking about serious global conflicts. That’s not what this is.


There are real rivalries out there that have real consequences and real tragedy attached to them, and that’s not what we’re doing here. This is show business. This is entertainment.


This is the stuff that, quite frankly, is fun to watch. It’s messy, it’s ridiculous, it’s sometimes petty beyond belief, and that’s exactly why we love it.


Because let’s face it, sometimes it’s just fun to sit back and watch rich, famous people yell at each other.


And there are so many different flavors of these rivalries.


You’ve got creative rivalries: people who worked together and then split apart and started taking shots at each other. You’ve got competitive rivalries: actors going up for the same roles, musicians competing for the top spot on the charts.


You’ve got personal rivalries: jealousy, betrayal, ego clashes, relationships gone bad. You’ve got sibling rivalries, which might be the most brutal of all, because those get deep and they get personal in ways that are just…uncomfortable.


And yeah, sometimes it’s funny. Sometimes it’s downright hilarious. People throwing out insults that are so over-the-top you can’t believe it. Sometimes it’s fascinating, like watching two brilliant artists try to outdo each other.


And sometimes…yeah, sometimes it crosses a line. Sometimes it gets ugly. Sometimes friendships end. Sometimes careers take hits. Sometimes it turns physical. And in at least one very famous case in the music world, it turned deadly.


But we still watch. We still read about it. We still pick sides. You do it, I do it, everybody does it. “I’m with this person.” “No, I’m with that person.” It’s like sports, but with actors and musicians and celebrities.


And there’s a weird relatability to it, too. Because even though these people live in a completely different world than we do, the emotions behind these rivalries (jealousy, competition, insecurity, anger) that stuff is universal.


And of course, there are tons of fictional rivalries that are legendary. I mean, come on...Luke Skywalker and Darth Vader, Rocky and Apollo Creed, Woody and Buzz Lightyear, Pac-Man and the ghosts, Jerry and Newman, Wile E. Coyote and the Road Runner…those are iconic.


But that’s not what this is about. This is about the real stuff. Real people. Real grudges. Real insults. Real fallout.


And in honor of the second season of Beef dropping on Netflix (which, by the way, is all about a rivalry that spirals completely out of control) I thought it would be the perfect time to look back at some of the greatest, most entertaining, most ridiculous, and sometimes most uncomfortable feuds in the history of show business.


There are a ton of them. I mean, I could’ve done 50 of these. Easily. But I narrowed it down to 15.


These are some of my favorites. They’re not ranked, they’re not in any particular order, they just represent the ones that I think are the most memorable, the most fascinating, and in many cases, the most entertaining to watch unfold.


So sit back, grab some popcorn, pick your sides, and enjoy the chaos.


Here are my 15 favorite entertainment rivalries of all time.


MY 15 FAVORITE ENTERTAINMENT RIVALRIES:


This is the gold standard. This is the heavyweight championship of Hollywood feuds. Two absolute legends who could not stand each other, and it went on for decades. It’s jealousy, it’s competition, it’s personal, it’s professional, it's everything.


And then you get Whatever Happened to Baby Jane?, where they’re forced to work together and basically channel all that hatred into the performances. It’s electric. It’s nasty. It’s legendary. This is the one everybody thinks of first, and for good reason.


This one is sad. Because for a while, they were magic together. One of the greatest comedy teams of all time. And then ego, control, resentment...all of it just blew it apart.


Jerry wanted more control, Dean wanted to be taken seriously, and boom. Done. They didn’t speak for years. Years. And when they finally reunited (on Jerry's MDA Telethon in 1976), it was emotional, it was awkward, it was real. This one still hurts a little.


Modern, messy, and absolutely unavoidable. It starts with that infamous moment at the MTV Video Music Awards (“I’mma let you finish…”) and it just spirals from there. Songs, tweets, interviews, lyrics, more songs, more tweets.


It’s like a never-ending cycle of public drama. And it’s a perfect example of how social media has turned these rivalries into 24/7 spectacles.


Late-night television turned into a battleground. This is behind-the-scenes corporate drama mixed with personal betrayal. Letterman thought he had the Tonight Show locked up, Leno gets it, and suddenly it’s war.


And then the whole Conan O’Brien mess years later just reopens the wounds. It’s fascinating because it’s not just about two guys, it’s also about networks, contracts, and the business of television. But yeah...Leno is a jerk, and Letterman rules.


Ah, the Battle of Britpop. This was a cultural event in the ‘90s. Two bands representing two different sides of England, two different attitudes, two completely different sounds, and they go head-to-head on the charts.


It was marketed like a prizefight. And the trash talk? Incredible. Liam Gallagher alone could fuel an entire rivalry by himself.


This one goes way beyond entertainment, it also became a cultural moment, and ultimately a tragedy. You’ve got Biggie on one side, Tupac on the other, and a whole lot of artists, labels, and media fueling the fire.


It starts as competition, it turns into hostility, and then it turns deadly. Two of the greatest artists of all time are gone. This is the darkest rivalry on the list.


Two brilliant writers who absolutely despised each other. And they didn’t hide it. Insults in print, insults on television, and yes, at one point, Mailer headbutts Vidal backstage. I mean, come on.


That’s next-level literary beef. It’s intellectual, it’s petty, it’s physical, it’s everything you want in a rivalry between two guys who are supposed to be above that sort of thing.


Two of the biggest figures in rock at the time, representing completely different philosophies. Axl is the larger-than-life rock god, Kurt is the anti-rock star. And they just do not like each other.


There’s tension, there are insults, there’s that infamous backstage encounter at the MTV Video Music Awards. It’s grunge versus glam, authenticity versus excess: pick your side (I'm clearly with Cobain).


This one is just bizarre. Lawsuits, accusations, stalking, countersuits... it's very messy in a very uncomfortable way. What starts as a relationship goes completely off the rails and turns into a very public, very strange legal battle. It’s one of those rivalries where you just kind of shake your head and go, “What is happening here?”


It did, however, result in a pretty great film called The Boost, which featured exceptional performances from both Woods and Young.


This is a long-running, very catty, very entertaining feud. Elton John has taken shots at Madonna for years (about her music, her performances, her lip-syncing) and he does not hold back. And Madonna, for the most part, just kind of lets him go. It’s one-sided in a way, but it’s still hilarious because Elton is just so blunt and so unapologetic about it.


See also: Madonna vs. Cher. Madonna vs. Lady Gaga. Madonna vs. Mariah Carey. Madonna vs. Janet Jackson. Madonna vs. Courtney Love. Madonna vs. Boy George....you get the idea.


God, I love Madonna.


This one is another sad one. Joan Rivers was one of Carson’s protégés, he gave her a huge break, and then when she took a competing late-night job without telling him, that was it. He felt betrayed, and he never spoke to her again. Ever. It’s a reminder of how personal these things can get, especially when loyalty is involved.


This is old-school Hollywood power struggle stuff. Welles makes Citizen Kane, which is clearly inspired by Hearst, and Hearst does everything he can to bury the movie. Ban it, suppress it, destroy it. And yet, here we are, Citizen Kane is considered one of the greatest films ever made. You don’t win that fight, Hearst. You just don’t.


Two massive egos, two legends, and zero patience for each other. They worked together on Guys and Dolls, and it was apparently miserable. Sinatra liked things quick and efficient, Brando was all about multiple takes and method acting. Sinatra hated it. Hated it. You can feel the tension in the movie, and honestly, it kind of works.


This one is infamous for a reason. The making of Chinatown was apparently a nightmare. Dunaway and Polanski clashed constantly, and it got personal, it got nasty. There are stories (some probably exaggerated, some probably not) that have become part of Hollywood legend. And yet, the result is one of the greatest films ever made. Go figure.


Van Halen fans, this is your civil war. Two completely different frontmen, two completely different eras of the band, and fans are still arguing about it. Roth is the wild showman, Hagar is the more "polished" rocker, and the tension between them (and with the band) has been ongoing for decades. It’s never really ended, and honestly, I don’t think it ever will.


By the way, I'm with Diamond Dave here...easily.



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