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20 Questionable Career Moves in Entertainment History

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Mel Gibson, you've just been arrested for drunk driving, accused Jews of starting all the wars in the world, and called a police officer sugar tits. What's are you doing next? I'm going to rehab!

So Mel likes his Dewars. So what's the big deal. I've had a few cocktails in my day. Actually, It's 7:00am now and I'm on my third shot. But that anti-semitic stuff...Max, that just doesn't play with the kids anymore. Hell, some people may even see this as an opportunity for ridicule, disparagement, insult, caricature, mockery, lampooning, parody, seventh inning rants or rap videos. And that movie you've got on deck...you know, the one filmed entirely in Mayan? Yeh, this could hurt the box office. You better lay low for a little while. Maybe come back strong with Lethal Weapon Twelve, or whatever number you're on. We'll call you when Ari calms down.

But Mel isn't the first celebrity to make a career threatening move. For every drunken rant in Hollywood, there have been ten other celebity misteps that don't involve a bartab. But they're just as painful...maybe more. So many in fact, that we couldn't keep it to ten this time. We've put together a list of twenty classic instances, where the star may have done things differently if given the chance. So take a look at twenty questionable career moves in entertainment history, because there's nothing more fun than a broke blogger making fun of millionaires for displaying poor judgement...Enjoy!

Well, would you do it for ONE...MILLION...DOLLARS
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Colin Quinn gets offered the role of Scott Evil in Austin Powers (a part written especially for him), but turns it down to work on an unfinished screenplay. This one's painful because a) Colin Quinn seems like a cool guy, and b) I think he would've been a riot as Dr. Evil's kid. But instead, Colin is working Artie roasts on Stern and Seth Green has a mansion in Malibu.


Hey, check it out. That guy looks like Hootie.
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Darius Rucker, lead singer of Hootie and the Blowfish, stars in a Burger King Tendercrisp Bacon Cheddar Ranch sandwich commercial. In the spot, Darius is outfitted in cowboy gear, and sings new lyrics to the tune of Big Rock Candy Mountain. Now I know Hootie wasn't actually setting the world on fire before this BK acid flashback spot, but did he really need to take the express train to VH1 clip show celebrity status? The outfit is the best part. Who knows, maybe he got a little dallas cheerleader action on the side.

Beautiful, loaded, and a little crazy? Dude, that is so hot.
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Winona Ryder gets arrested for shoplifting thousands of dollars worth of designer clothes at Saks Fifth Avenue in Beverly Hills. The star is sentenced to three years' probation and 480 hours of community service.. Actually, it's not the shoplifting that amazes me (that's a rich girl thing), or the fact that she had an entire pharmacy in her purse. But reading recently that she's a nymphomaniac...there's your jackpot. By the way, while we're on the subject of genius moves, Johnny Depp getting a Winona Forever tattoo wasn't too bright. Isn't that tattoo rule #1, or something.


And tell the masterbating bear to go screw himself, too.
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After seven seasons of helping build Late Night with Conan O'Brien into a cult comedy hit, sidekick Andy Richter leaves to pursue an acting career. Hey, that Andy Richter controls the universe show lasted a while, didn't it? Howard Stern had a field day with this one, but I actually admire Andy for leaving the nest. No one wants to play second fiddle forever. And besides, if he hadn't left, we might have missed the funniest scene to ever come out of the Scary Movie franchise.


The Sharon Stone curse strikes again.
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Three years after Halle Berry gives an oscar winning performance in Monster's Ball, she wins a Razzy award for worst performance of the year in Catwoman. Yeh, that's a good look. And you can save the mask if you ever do any S&M flicks. Ms. Berry took it in stride though, actually making a surprise appearance to accept ther razzy, and thanking the producers for putting her in a "God-awful movie”. So it's nice to know she's got a sense of humor about herself.


If David Caruso can do it, I sure as hell can.
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After five seasons, Shelley Long leaves the cast of Cheers to pursue a career in film. Her first project after leaving the show, Troop Beverly Hills makes 5 million at the box office. Shelley should be the spokesperson for Bad Career Choice Magazine, as her case is always the one mentioned when it comes to poor tv-to-movie decisions. Cheers lasted six more seasons, but Shelley did go on to make The Brady Bunch in the White House, so who's laughing now?


I don't know. I just don't think the political schtick will last.
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Craig Kilborn leaves The Daily Show after three seasons to host the CBS Late Late show. Then leaves the CBS show to shift to a career behind the scenes as a writer. Hey look, a two-time winner. I'll bet you forgot Craig Kilborn was the original host of the Daily Show. But if he left the late night gig to be a writer, why has he taken supporting roles in Shaggy Dog and The Benchwarmers. I never liked Kilborn, he definitely hung with the cool crowd in high school. Guys like that bother me. By the way, check out the correspondents in those early years. And what about how young Stewart looks when the torch get passed...pretty funny.


I think I'm gonna pass. I like this talking snowman script.
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After appearing in two Batman movies, Michael Keaton decides to pass on the remaining films in the franchise, possibly out of concern about being typecast, or that he'd be upstaged by Jim Carrey. Keaton's whole career has been a mystery to me. He goes from Night Shift and Mr. Mom, to Batman and that freak in Pacific Heights, and now back to nice guy in Jack Frost and Herbie Fully Loaded. He's like Cybil with a receeding hairline. It would've been cool if he stayed with Batman, though. If nothing else, it would've taken a black mark off of Clooney's resume.


I'll show them. They can't buy Juliana Marguilies. I've got Ghost Ship money.
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Juliana Marguilies turns down a contract valued at a reported $27 million to return for two more seasons on the hit series ER, choosing instead to seek different and challenging roles. I actually respect the hell out of this decision. I'd never mirror this decision, but I respect the hell out of it. Can you even imagine turning down 27 million dollars? Can you imagine turning down 2,700 dollar? Can you imagine turning down 27 dollars? Do you have an imagination? Next up for the woman with the mad integrity...mother fucking snakes on a mother fucking plane...hot damn.


Retag...Retain...Retake...here it is, retarded. Yup, there's Hugh Grant.
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Hugh Grant is arrested near Sunset Boulevard in Hollywood, having been caught receiving oral sex from prostitute, Divine Brown, in the front seat of his car. How does a guy give up this, for this. It's one of the great mysteries of the universe. BUT, and this is a big but, he performed the biggest publicity turnaround in history by going on every show he could think of to apologize. No seclusion for Mr. Grant...someone get me Jay Leno on the phone. And Leno was thankful, since it was the Hugh Grant interview that finally pushed the Tonight Show ahead of Letterman. And Mr. Grant takes his rightful place in the celebrity mugshot hall of fame.


Let'em try to replace me. I'm Alec mother f'in Baldwin!
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Alec Baldwin stars as Jack Ryan in Hunt for Red October, then shocks Hollywood by not starring in the sequel because of a dispute with Paramount Pictures over money and script changes. Got no problems with this one, as Alec Baldwin is one of my all-time favorite actors. Screw the studio is they can't see things the Baldwin way. SNL host 183 times, and each one funnier than the last. And have you ever seen his cameo in GlenGary Glen Ross...f'ing awesome. I can't wait for the new NBC show. So, who needs Patriot Games money. He's done The Simpsons, dammit.


Matrix, Schmatrix...The Western script has a big mechanical spider?
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Before it was given to Keanu Reeves, Will Smith is offered the lead role in The Matrix and turns it down to star in Wild Wild West. If anyone's got Will Smith's phone number, can I get it from you? He still owes me the ten bucks I paid to see that flick. On second thought, forget it. He did do Ali. But think about how different Matrix would've been if Will Smith was Neo, Sean Connery was Morpheus, and Dakota Fanning was Trinity (made that one up). By the way, that's my photoshop job...can you believe the skills?


And please welcome our sixth band member...splity spice.
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Michelle Stephenson is hired as one of the original five Spice Girls, but leaves to pursue other interests, and is replaced by Emma Bunton. Hey look, Pete Best with long hair. You didn't even know who this was, did you. Neither did I...no one does. Ergo, the lovely woman's inclusion on this list. Michelle left just before the girls came out with Wannabe...pretty poor timing on her part. This one's not actually a career changer. More like a potential career stopper. But that's another list. Check back for that one next week.


Actually, I think it was Robin's laugh that drove him away.
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Longtime Howard Stern show regular Jackie "The Jokeman" Martling leaves the radio show after failed contract negotiations, and is replaced by comedian Artie Lange. Anyone heard from Jackie since he left the show? I know he did that one appearance before the Sirius move, but anything other than that? No, I didn't think so. I was in upstate NY about a year ago for the holidays, and I happened to go into a Spencer Gifts (see if it had changed any since high school) and there's this Jackie joke-telling toilet paper holding thing. That pretty much sums up the results of this clasic career faux-pas. Howard was recently listed as the second richest celebrity IN THE WORLD. So how much do you think Artie makes? That could've been Jackie's. Yeah, he's not bitter.


Points on this piece of crap? Thanks, but I'll take the cash.
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Donald Sutherland takes a small role in Animal House, requiring two days work. Sutherland is offered either a $40,000 flat fee or a percentage of the film's gross...he opts for the flat fee. A decision which cost him over 30 million dollars. In Donald's defense, they did find pods in his basement before filming began, so who knows what was going on. This is a classic Hollywood story. What would you have done? Everyone from Chevy Chase to Bill Murray had passed on the flick, so it didn't have that promising a start. Oh well...spilt milk and all. Hey, you ever seen Kelly's Heroes...great flick.


So many bad decisions. So little time.
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Ben Affleck stars in Gigli. That's all on that one.


Cute Kelly Ripa doll collection...what's with the pins?
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Perky talk show host Kathie Lee Gifford announces she's leaving Live! With Regis and Kathie Lee after 15 years of engaging morning coffee klatches. Kathie Lee explains that she's worried about co-host Regis Philbin, who has been moonlighting for the runaway success Who Wants to be a Millionaire, saying that he's too tired and the audience deserves better. There are some of these that the stars regret...and then there are some of these that the stars REGRET. I can't even imagine how Frank takes it day after day. If Cody and Cassidy don't start walking some red carpets with mommy, she may have to start pitching a variety show with some of those Malaysian ten year olds. Watch your back, Kelly. Nobody puts baby in a corner.


Poor guy...never had much of a career after that.
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Gary Cooper turns down the role of Rhett Butler, saying Gone With The Wind will be the biggest flop in Hollywood history. I included this just because I wanted one old one. And it's actually pretty interesting. But when you consider Pride of the Yankees, Sergeant York, High Noon and about fifty other flicks, I think he made out ok. Separate note...Gary Cooper died at age 60 of lung cancer. There's a poor career move on an entirly different level.


Tell him Indiana wears a Hawaiian shirt or the deal's off.
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Tom Selleck is cast as Indiana Jones in Raiders of the Lost Ark but is forced to decline the role due to scheduling conflicts with Magnum PI. The movie is filmed with Harison Ford, and shooting eventually wraps before Magnum production begins. This may be more of a Magnum's producers thing than a Selleck thing. Either way, I'll bet Tom's kicking himself. Because I don't think High Road to China did quite as well. Let that be a lesson to you, kids. Always check your dates. Come to think of it, he was in Hawaii at the time...maybe it was a time zone thing.


I just saved a bunch of money on my car insurance by...
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Tom Cruise fires his long-time Hollywood publicist, Pat Kingsley after 14 years of working together, and hires his own sister as a replacement. Mr. Cruise then proceeds to go nuts. Here at YesBut, we love Tom Cruise. But really, who doesn't. If he's not jumping on Oprah's couch, he's telling Matt Lauer how glib he is. And I think you'll agree, both are things that needed to be done. Between battles with the South Park Boys and hiding Katie and the kid, where does he find time to make bad action flicks? Then again, I have no idea how a high level thetan really operates, so maybe I'll just shut up before men in black coats start bangin on the front door. Good work Tom...and tell sis she's doing a great job, too!


And that's it for the bad decision list. There were probably dozens I forgot, but twenty's good for a start. Please write in to say which ones I missed...you always do.

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35 Comments

Whew, 20 of them huh? That's going to make it a lot harder for the "Hey Asshole, How Could You Have Left Out (Insert Same Example Already Mentioned Two Comments Up)?" Crowd.

said Evil Richard on August 17, 2006 1:28 PM.

Well I think technically Craig Kilborn's contract was not renewed for The Daily Show so I don't think that was his fault. I could be wrong though.

said Suzanne on August 17, 2006 2:41 PM.

I think your picture of Michelle Stephenson is actually one of the real Spice Girls (Sporty)...although you're right about the rest of the story.

said maybenot on August 17, 2006 2:54 PM.

Whoops...I thought they looked similar. Thanks for the heads up. But Kilborn leaving was definitely his decision. CBS was looking for a Tom Snyder replacement, and he wanted the job.

said Jellio on August 17, 2006 3:47 PM.

totally disagree about Michael Keaton. smart move not to star in Joel Schumacher's embarrassing Batman sequels, two of the worst movies I've ever seen. maybe his career took a turn for the worse afterward, but maybe, for him, it would have taken a complete nosedive had he continued with Batman.

said SS on August 17, 2006 5:29 PM.

Yeh, but I think that was my point. The sequels might have been better, or stayed a little darker, had he stayed on. Definitely not a given though, I agree.

said Jellio on August 17, 2006 5:46 PM.

I hear after Keaton turned down Batman, he was blackballed in Hollywood by the JEWS.

said Mel Gibson on August 17, 2006 6:03 PM.

Speaking of Spice Girls (the thought of the group as a whole either makes me physically ill or points my rod north, depending on which one I'm thinking of at the time), I think it was a pretty poor career move for Geri Halliwell to leave... not so much for her, but for the rest of the band! At least she was still a bit popular on her own, the rest of the band kind of faded into trivia queation purgatory. Also, Geri was and is pretty smokin' hot.

said Dr. Strangelove on August 17, 2006 6:34 PM.

Kilborn left for a shit-pot full of money. Comedy Central was offering about 1/5 of what CBS paid him. How can you criticize him for doing that, when you turnaround and criticize Juliana Marguilies for passing on the money a couple of paragraphs later?

said deeoh on August 17, 2006 7:50 PM.

I think I said I respect Ms. Marguilies' decision not to take the money. And none of these are criticisms, just asking if the celebrities might have handled things differently if given the opportunity.

said Jellio on August 17, 2006 8:30 PM.

A few more:

David Caruso left NYPD Blue after one season for a movie career that went into the toilet save for one film Kiss of Death. Got a second chance though with CSI: Miami.

Dougray Scott was signed to play Wolverine in the first X-Men, but conflicts with Mission Impossible II forced him out and produced a last minute replacement with Hugh Jackman. Tony Award winning actor Hugh Jackman.

Chevy Chase leaves SNL after one season. Now he is joke fodder for the new movie, Accepted.

Jeffrey Hunter, who played Captain Christopher Pike in the first Star Trek pilot The Cage, turned down an offer to star in the second pilot. His career was never the same after that. At least he didn't become the object d'ridicule on a Comedy Central Roast.

John Wayne turned down the role of Patton. Obviously it would've tarnished his liberal left-wing image...

said Miami Spice on August 17, 2006 10:36 PM.

Michael Keaton left Batman after the first two, because A) Tim Burton was taken off the project (he first took Batman as a favor for him) and B) He wanted like 15 mil to do the movie.

Well when you see Jack Nick make like 40 mil ($6 mil plus percentage) from the Batman movie, would'nt you want your slice of the pie?

said Rdot on August 17, 2006 10:40 PM.

You forgot the part where I appologized, and the part where Jon Stewart was a Jew... A BLOODY JEW! HOW CAN YOU PEOPLE EVEN STAND TO LOOK AT THIS MAN?

Mel_Gibsy@gmail.com

said The REAL Mel Gibson on August 17, 2006 11:54 PM.

I can understand the majority of those as bad decisions, but Michael Keaton made a great choice. Batman Forever and Batman and Robin are examples of a great series gone bad. Not only did they take away the director that made the successful, but they changed the Dark Knight into a colorful Neon Bat. Thankfully Batman Begins brought the franchise back to it's roots...

said Adibobea on August 18, 2006 2:23 AM.

Dave Chappelle turning down the role of Bubba in 'Forrest Gump' is a good one to add to this list.

said choco6 on August 18, 2006 2:03 PM.

You know, now that you mention it, the Chappelle Africa trip could have been a biggie on the list.

said Jellio on August 18, 2006 3:12 PM.

you forgot the biggest oops ever! George Raft (who?)
turned down Humphrey Bogart's part in High Sierra first, then turned down Bogart's part in The Maltese Falcon. OOPS!

said your big oops on August 20, 2006 2:43 AM.

Eddie Murphy turned down Rush Hour to do Holy Man.

said Justin on August 21, 2006 4:34 PM.

Your expose on Jackie Martling claims that “Howard [Stern] was recently listed as the second richest celebrity IN THE WORLD.” Stern was actually listed as the second highest earning celebrity in 2005. There is a HUGE difference.

said Buck on August 21, 2006 8:16 PM.

What about Chevy Chase being originally approached for both American Beauty AND Lost in Translation?? God, that guys career is the pinacle of bad choices.

said kevin on August 21, 2006 10:37 PM.

Actually Sofia Coppola has alwasy stated the Bill Murray was her one and only choice for Lost in Translation, don't know about American Beauty

said roche on August 22, 2006 11:48 AM.

this is what Michelle Stephenson looks like:
http://alberworld.blogcindario.com/ficheros/sg06-michelle.jpg

said Spaulding Smails on August 22, 2006 12:00 PM.

That picture of 'Michelle Stephenson' is definitely a pic of Sporty Spice (Mel C).

said daisy2316 on August 22, 2006 1:34 PM.

To be added to this list in the next 5 years -

Dave Chappel turns down $50mm for one more season on Comedy Central and then realizes his 10 min of fame are over. I love Dave and all, but damn.

said killing it on August 22, 2006 7:32 PM.

Keaton also turned down the lead role of Jack on "Lost", because originally the character was suppose to die in episode 1, but after the writers kept him alive he opted out.

said Ryan on August 23, 2006 1:26 AM.

Posted by Spaulding Smails.

That picture of 'Michelle Stephenson' is definitely a pic of Sporty Spice (Mel C).


The fact that you know this makes you hopelessly pathetic.

said Nunya on August 27, 2006 12:03 AM.

Great list. Unfortunately you don't know how to spell "masturbate", which makes this read like it was written by a sixth-grader.

said Gobo on September 11, 2006 1:02 PM.

hello,all

said guest1982 on March 30, 2007 8:27 AM.

Jackie hasn't been heard from? Uh,no that's not true. He's doing his Sirius show on Howard 101 and standup all over. And he is so hot...that was always the secret.

said If*ckedJackieMartling on May 9, 2007 10:37 PM.

Oooo...don't forget Paul Reuben (Pee Wee Herman) masturbating in a public porno theater. That got his show canceled. That belongs riht next to Hugh Grant.

said Pee Wee on May 24, 2007 6:56 PM.

Very interesting site. Hope it will always be alive!

where are you google, i miss you?

said Saher1979 on June 7, 2007 12:40 PM.

Very interesting site. Hope it will always be alive!

where are you google, i miss you?

said Saher1979 on June 7, 2007 12:40 PM.

Keep working!

where are you google, i miss you?

said Saher1979 on June 10, 2007 8:32 AM.

Great site. Keep doing.

where are you google? i miss you!

said Johnjidf on June 11, 2007 9:13 AM.

Awesome list, thanks.
I agree that Keaton leaving the Batman movies was a good idea; his roll in Much Ado About Nothing is still one of my favs.
Will Smith as Neo in Matrix, would have made it a different and possibly better movie...(although the first Matrix is quite decent).
I think Passion of Teh Christ was the movie that announced Mel Gibson's fall.... I mean wtf... it was just Braveheart in the desert, now with Extra Suck and 25% more Blasphemy... (Christians are so easily entertained and fooled out of their money when they think other Christians are judging them); the book is better!

What about a post/list about movies/projects that saved/reinvented careers . . .

said twitchings.livejournal.com on April 8, 2008 10:50 AM.
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