Everyone makes mistakes both in their everyday lives and in their careers. It shouldn’t come as any surprise that sometimes the people making those mistakes are professional actors, and often among the best and most respected in their fields.
Some actors have an amazing track record for picking great scripts whether they’re just incredibly selective or simply have great taste. For other actors, that track record isn’t always so great. Whether they make bad decisions based on money, doing favors for friends, or simply having no idea what they’re doing, it can be pretty amazing just how bad some of those choices get to be now and then.
16Tiptoes – Gary Oldman
One of the most infamously baffling movies in recent history, Tiptoes has a heck of a cast but somehow puts Gary Oldman in the role of a little person, and is notorious for being one of the most unintentionally hilarious movies to come down the pike in awile.
15The Love Guru – Ben Kingsley
Sir Ben Kingsley is an incredibly well-regarded actor who gained fame and an Oscar for playing Gandhi, but if you ask us his appearance in the terrible “comedy” The Love Guru should because for him to give that Academy Award right back.
14The Adventures of Rocky and Bullwinkle – Robert De Niro
Robert De Niro has made some pretty baffling career decisions, but none more so than one of his first attempts at family comedy with the live action adaptation of Rocky and Bullwinkle.
13Jack and Jill – Al Pacino
Because we can’t talk about De Niro without mentioning Pacino, we have to put the abysmal Jack and Jill is here with a special mention of Gigli, meaning that the man who played Michael Corleone has been in literally two of the worst movies in history.
12Jaws: The Revenge – Michael Caine
To his everlasting credit, Michael Caine has famously quipped that he’s never actually seen Jaws: The Revenge – which is a great so-bad it’s a hilarious film – but he has seen the massive house it built, so at least he’s happy to admit he did it all for the paycheck.
11Man of the House – Tommy Lee Jones
Wouldn’t you have loved being in the room when someone convinced Tommy Lee Jones that it would be a good idea to do a movie in which he’s an undercover officer posing as the coach of a cheerleading squad?
10The Jerky Boys – Alan Arkin
In fairness, Alan Arkin wasn’t quite as well regarded back when the Jerky Boys came out, but he was still known and well-liked, and it’s just a little sad looking back now and realizing he had to subject himself to crap like this.
9Bride Wars – Anne Hathaway
Whether you love or hate Anne Hathaway, it’s hard to argue that she’s not a great, respected actress – which makes her appearance in the horrific Bride Wars all the more unfathomable, despite the fact that she’s rebounded pretty nicely and won an Oscar along the way.
8The Bucket List – Morgan Freeman
We could actually toss Jack Nicholson in here as well, but whichever one of these all-time great actors we choose for this entry no doubt looks back and wonders what the hell they were possibly thinking by signing on the dotted line.
7Little Fockers – Distin Hoffman
Meet the Parents was a smashing success so it’s no secret that it spawned a sequel, but then it just kept spawning tired retreads and, at some point, you have to think that someone like the great Dustin Hoffman had to stop and wonder what on earth he was even doing anymore.
6Krippendorf’s Tribe – Richard Dreyfuss
Let’s be honest, you don’t even have to know what this movie is about, and can simply look at that movie poster to realize that holy crap, this was just a tremendously poor decision by Richard Dreyfuss.
5She-Devil – Meryl Streep
Even the legendary Meryl Streep isn’t immune to making terrible movies now and then, as evidenced by the inexplicable decision by the Oscar luminary deciding to share the big screen with Roseanne Barr.
4The Chronicles of Riddick – Jido Dench
And no, not even the British answer to Meryl Streep, the one and only Dame Judi Dench, can avoid the occasional bizarre movie choice – this time appearing alongside Vin Diesel in the overblown space opera sequel to the far superior Pitch Black.
3King Ralph – Peter O’Toole
For those too young to remember, Peter O’Toole became an icon for, among other things, playing Lawrence of Arabia, yet at some point, it apparently became necessary for him to star alongside John Goodman – who we love, mind you – in this terrible movie about an American slob who becomes King of England.
2The League of Extraordinary Gentlemen – Sean Connery
It’s been long rumored that the only reason Sir Sean Connery, the former James Bond himself, only chose to star in The League of Extraordinary Gentlemen because he was furious with himself for passing on Lord of the Rings and the Matrix and didn’t want to miss out on another possible smash hit.
1The Island of Dr. Moreau – Marlon Brando
Arguably the most embarrassing performance on this entire list, it says something when the most lasting impression of Brando’s role in The Island of Dr. Moreau is the strange character it inspired on the television show South Park.