20 Famous Actors That Starred In Incredibly Embarrassing Early Roles

It's probably not a good idea to revisit these, unless you want to die of laughter...

Every actor has to start somewhere. Even those who started out as children had to have that first role, that first commercial, that first uncredited background part. And when you’re a struggling actor trying to find that breakout moment, it’s easy to get desperate enough to take any role that comes your way.

That’s probably why so many of your favourite actors started out in films and television shows that are nothing short of cringeworthy. Most of them would probably prefer it if the world as a whole forgot about these early roles, since they are so embarrassing – especially when you know what a superstar the actor in question was destined to become.

You may be shocked to find out that some of your favourite actors weren’t always so smooth. The heartthrob was once a quickly dispatched dumb character in a teen horror flick. The serious actor once had to put on a silly wig and act the fool for a children’s show. And the goofy, greasy comedian once took a part as a thug who was supposed to scare the audience. Knowing who they are today makes these roles all the funnier!

If they had their way, you would never even know that these prime pieces of film and television existed. Thankfully, we do. Here are 20 examples of superstar actors taking on roles that they would look back on with shame – and which you can still watch today, if you want to have a laugh at their embarrassing antics!

20 Kate Winslet & Daniel Craig - A Kid In King Arthur’s Court


This movie certainly belongs on the list for starring not just one, but two superstars before they were really all that famous. In 1995, Kate wasn’t yet Rose, and Craig wasn’t yet Bond. That’s probably why they ended up in this shocker of a film, which has an incredible 6% rating on Rotten Tomatoes. Really, that in itself is enough to make it noteworthy. How many other films do you reckon could star two of the biggest Hollywood actors of the 21st century and still manage a rating that low? It was based on Mark Twain’s A Connecticut Yankee in King Arthur’s Court, in case you were wondering.

19 Matt Damon - Mystic Pizza


This is one of those films that isn’t so bad in itself – it’s more the problem of who was in it. This is the first big role Matt Damon got his hands on, and though he only has one speaking line, he is rubbing shoulders with the kind of stars who would later be his peers. Of course, that line in itself is enough to induce a cringe: he asks his mother if she would like to eat his “green stuff.” Stunning writing, there, matched only by the delivery. Bless least he would go on to better things eventually.

18 Nicolas Cage - Fast Times at Ridgemont High


Now, before anyone gets all worked up, we’re not saying there’s anything bad about Fast Times at Ridgemont High. It’s a classic teen 80s movie, just like The Breakfast Club or Pretty in Pink. The one thing it has that those two titles don’t however, is Nicolas Cage. Yes, that Nicolas Cage. The one with the bees. He’s got a lot to be embarrassed about in his career, but the big thing with this movie is how far it is from his usual material, even when you take into account his famous inability to stick to good scripts only. This is a bit of an odd turn for a man best known for shouting really angrily and chewing the scenery as much as possible.

17 Courteney Cox - Masters of the Universe


1987 was a time before Friends, and much like her co-star Jennifer Aniston (more on that later), Courteney Cox was looking for a movie role and wasn’t too discerning about it. She wound up starring in the critical and commercial failure Masters of the Universe, based on the adventures of He-Man. It ran over budget, was accused of hiding a gay love story, and bombed within a week of release. It didn’t even make back the money that the studio put in. Ouch. Of course, with Friends and Scream under her belt, Cox can at least feel proud of her career after that point.

16 Paul Rudd - Halloween: The Curse of Michael Myers


This series is one of the worst offenders out there for churning out pointless sequels, and just about the only good thing you can say about this is that it’s a chance to watch Paul Rudd in action before he knew he was going to be, well, Paul Rudd. It was released in 1995 and was the sixth movie in the series, with Rudd playing a character called Tommy Doyle. You may recognize the name as being the kid from the first movie: he is supposed to be a grown-up version, and that’s about as much research we could bring ourselves to do into this waste of screen time.

15 Jake Gyllenhaal - City Slickers


Imagine Jake Gyllenhaal. Yes, I know what comes to your mind: a brooding hunk, ripped abs and all, tackling war films and nerdy roles with equal vigour. The ultimate alternative leading man. Now, cast your mind back to the 90s, when City Slickers first came out. There was a 10-year-old kid in that movie goofing around, generally relying on the acting technique of pulling a really silly face so everyone would laugh. That kid was Jake Gyllenhaal. He may not mind taking on the outsider roles, but this one is something we’d bet he wouldn’t mind scrubbing off his CV.

14 Laurence Fishburne - Pee-Wee’s Playhouse


It’s not likely that you would imagine a link between Fishburne and Pee-Wee Herman. But, in fact, they shared the screen together at one stage, while Fishburne was playing his Cowboy Curtis character. He was one of the regular characters on the show, dressed up in an outrageous cowboy costume including a pink shirt, a waistcoat, and a fetching hat. His role involved special moments like singing songs for the audience, which certainly jars against his later serious work. It’s difficult to picture Morpheus being a children’s entertainer, for example. It’s also a fairly embarrassing look for anyone to have rocked.

13 Morgan Freeman - The Electric Company


Morgan Freeman is another serious actor who once had to make ends meet with something a little less serious. With a great sense of humour it’s unlikely that he would feel embarrassed about his role on The Electric Company, but maybe he should! He played the character of Easy Reader on this 1970s children’s TV show, and the name wasn’t the only terrible thing about it. He sported dark sunglasses, a neat little ‘fro, and a lumberjack shirt to present words to the kids watching at home. Very far from Shawshank Redemption, the role that helped him really break out.

12 Quentin Tarantino - The Golden Girls

Quentin Tarantino is the master of blood spray. The director, who is unafraid to push boundaries, serves as a visionary who occasionally inserts himself into the movie as an actor. If you have very good eyes and for some reason only have access to the television of the 80s, you might notice his presence in the Nov. 9, 1988 episode of The Golden Girls, titled "Sophia’s Wedding (Part 1)." A bunch of impersonators show up in this episode, and sure enough, Mr. Tarantino is among them. He’s even listed in the credits in case you were unsure and needed proof.

11 Leonard Nimoy - Zombies of the Stratosphere


I mean, it’s almost as if you don’t need to know any further details. Leonard Nimoy, he of Star Trek fame, was once in a movie called Zombies of the Stratosphere. You can tell immediately that it was never going to be a classic. Or at least, not for any of the right reasons. Want more? Okay, how about the fact that his character was an evil Martian agent called Narab? Or that it was released in 1952? Poor Nimoy was only 21 at the time, and obviously had no idea that people would one day be able to track down his shameful early work via the internet.

10 Michelle Williams - Baywatch


Back in 1993, Baywatch seemed kind of like the best thing since sliced bread. It was a simpler time. We just didn’t know. Anyway, these days it seems horrifically dated – everything from the fashion to the grainy recordings to the use of "the Hoff" in an actual genuine acting role is just so passé. Imagine the horror, then, that faces a 13-year-old Michelle Williams when she was cast to star opposite Hasselhoff and his on-screen son. Admire this amazing video clip, in which she slowly and awkwardly runs along the beach in a bikini, for no reason, except to create a reason for the characters to talk to her.

9 Tom Hanks - He Knows You’re Alone


How many times do we see a big star who started off in an awful teen slasher? Way too many – so budding actors, take note. You might be desperate for the money, but it will come back to embarrass you later in your career. Much better to leave the slashers to those with no ambition. Tom Hanks most likely regrets starring in this 1980 cheese-fest, although there was some inkling of his later star power; the director rewrote his role to keep the character alive after liking his performance too much to let him get killed off. His next film after this was the breakout Splash.

8 Joseph Gordon-Levitt - Roseanne


It’s sometimes difficult to remember that Gordon-Levitt didn’t appear on the acting scene as an adult, but as a child. He certainly has a very different look to what he previously had, and has also changed his personal image in order to take on different kinds of roles. But between 1993 and 1995, before the greasy-haired teenager on 3rd Rock From the Sun, he was the annoying young neighbour called George on Roseanne. He only appeared in four episodes, but it’s pretty hilarious to see the young boy he used to be – particularly compared to his more macho turns in movies like Don Jon.

7 Jack Black - Never-Ending Story


Now, let’s get it straight: 1994’s Never Ending Story is a children’s classic. Which is why it’s such a shame that you won’t be able to watch it in the same light now that Jack Black is as famous as he is. In this film, he played the leader of the Nasties in his early career. The character, Slip, was supposed to be a high school bully who was seriously intimidating to our heroes. Instead, it’s hard to not find it very funny now that you know him as the man from Tenacious D, Nacho Libre, and School of Rock.

6 Ryan Gosling - Are You Afraid of the Dark?


The year was 1995, and 15-year-old Ryan Gosling had left the Mouseketeers (which is embarrassing enough) to return to his native Canada. Fellow alumni Britney Spears and Justin Timberlake seemed destined for great success, and yet Gosling couldn’t seem to grab onto that same opportunity. He took a role on TV series Are You Afraid of the Dark? for one episode, "The Tale of Station 109.1." His character was Jamie Leary, and it’s pretty funny to see him playing a role that is not just ridiculous, but also fairly out of the scope of his normal roles. Not to mention his 90s haircut and clothing.

5 Jennifer Aniston - Leprechaun


As far as cringeworthy roles go, camp horror flicks have to be right at the top of the list. Is there ever an appropriate time to get involved in a low-budget slasher? This example is particularly embarrassing for Jennifer, who spent 92 minutes of precious time on screen as Tory Redding, the main character. This movie about an evil leprechaun who vows to kill as many people as he can to get back his pot of gold has something of a cult status these days, but not because of how good it is. Thankfully for her, Aniston later went on to star in Friends and put these low-budget moments behind her.

4 Johnny Depp - A Nightmare on Elm Street


By now, most people know about the early appearance of Johnny Depp in A Nightmare on Elm Street, but that doesn’t make it any less cringe-inducing. First there’s the fashion – his borderline homoerotic belly-flashing outfit is really an artifact of its time. This 1984 flick is also notable for offing newbie Depp’s character as just another teenage victim of the slasher genre. Really? Even though he wasn’t quite the superstar we now know yet, it should have been clear from the outset that Depp is the kind of leading man that survives to the end, if only by looks alone.

3 Sylvester Stallone - The Party at Kitty and Stud’s


In 1970, Stallone was truly at a low point. He later said, “It was either do that movie or rob someone because I was at the end – at the very end – of my rope. Instead of doing something desperate, I worked two days for $200 and got myself out of the bus station.” So what was so awful about the movie that he was forced to take on? Well… it was a softcore adult movie, for a start. This was Sly’s film debut, and a very unfortunate one at that. The producers could hardly know that their lead star would later be Hollywood A-List.

2 Jean Claude Van Damme - Monaco Forever


Jean Claude’s first role was flawed, to say the least. All you really need to know is what you can learn from the credits, first of all the fact that they called him “Jean Claude Vandam.” Secondly, his character name. It’s not uncommon for a background or minor character to be named by a description, and that’s fine. It’s just not usually as embarrassing as this one. JCVD ends up being credited in this film as… wait for it… “Gay Karate Man.” Truly, the credit to end all credits. You probably don’t need to watch the film to know not to expect greatness.

1 Matthew McConaughey & Renee Zellweger - The Texas Chainsaw Massacre: The Next Generation


Back in 1994, we didn’t know the names McConaughey and Zellweger. These two were just struggling actors, trying to get their foot on the ladder of the acting world. For some reason, both of their agents decided it would be a really good idea for them to star in a Texas Chainsaw Massacre sequel called The Next Generation, known to fans as “the one where Leatherface wears a dress”. We’re not saying the film was awful, but McConaughey’s management actually had the release delayed until 1997 and ensured it went straight to video rather than showing in cinemas because of the damage it could have done to his then-fledgling career. Not only are they certainly embarrassed by it, but they didn’t even want it to come out!

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20 Famous Actors That Starred In Incredibly Embarrassing Early Roles