All The Times Chris Pine Showed His Weird Side

Giorgio Armani 40th Anniversary - Silos Opening And Cocktail Reception - Arrivals
Getty Image

When you power-binge the new Wet Hot American Summer series after it debuts on Netflix this Friday, you’ll not only see the entire original cast, but a few new faces. Some are great, recognizable additions like Kristen Wiig and king of the comedy cameo Jon Hamm, but one name that probably surprises a few people is the newly-announced love interest of Wonder Woman, Chris Pine. Generally known for his leading man/action roles like Captain Kirk in the rebooted Star Trek series, Pine is actually adept at shedding that facade and giving up vanity to play some really weird roles while still maintaining his burgeoning blockbuster career. Putting his mainstream resume aside, Pine is not only a really talented comedic actor, but he’s also a chameleon who can make you forget he was ever in The Princess Diaries 2.

Here are some of his best, weirdest roles to date:


If you want a real introduction to non-heartthrob Chris Pine, Joe Carnahan’s Stretch is the first movie you should watch. Not only is it on Netflix, ready to stream, but you will really not believe this is the same guy manning the Enterprise. Bearded and basically naked right off the bat, an unrecognizable Pine plays Roger Karos, an eccentric millionaire who says he’ll pay off the gambling debt of Patrick Wilson’s limo driver character if he carts him around without asking any questions. Which means there will be many, many questions about what Karos is doing and how he rolls. This movie is Pine at his most bizarre, and, like the title, it’s his biggest stretch as an actor. He’d never win awards for this kind of movie, but if he can disappear that effectively into such a wack job, he can disappear into anything.

Smokin’ Aces

Way back in 2006, Chris Pine slipped into the character of neo-nazi punkass Darwin Tremor in Smokin’ Aces. This was the first time Pine worked with Carnahan, and he should work with him one million and five more times, at least. Carnahan seems bent on making Pine look as unattractive as possible, and then getting him to chew scenery and make a nasty little spectacle of himself. It’s easy for Pine to slip by anonymously among this bevy of stars — Alicia Keys in her film debut, Common, Ben Affleck, Ryan Reynolds, Taraji P. Henson, Jason Bateman, to name a few — but he still stands out for being rude, crude, and pretty damn disturbing. And the owner of one of the filthiest (fake) tattoos I’ve ever seen.

Celeste and Jesse Forever

In case you needed an excuse to watch this amazing movie, knowing that Chris Pine is in it, credited as “Kris Pino” and playing a silent character named “Rory Shenandoah” in exactly one scene, here is your excuse! Knowing who Pine is makes this cameo a real WTF moment because it could have been anyone. It could have been someone less famous, or not famous at all. But the fact that it was Chris Pine makes it a seriously random bright spot in a really heartbreaking movie.

Funny or Die’s “Vampire Lawyer”/Chaz Benjamin (“Pa-gents”)

In the midst of his post-Star Trek fame, Pine did a couple of sketches for Funny or Die… an old-school send up of lawyer shows, “Vampire Lawyer” and the beauty pageant reality show spoof “Pa-gents.” I wish I knew the story behind these, but I don’t. I would have to assume that the people who made these videos are Pine’s friends — apparently, he prefers to keep company with a non-famous crowd of old friends, just another reason to like Chris Pine — and he stepped in because he’s just that cool to not care about his movie star image to have a little uber-indie fun.

[protected-iframe id=”d3d9d312b381a39591ff9ec0d434580b-60970621-61885062″ info=”″ width=”640″ height=”400″ frameborder=”0″ webkitallowfullscreen=”” mozallowfullscreen=”” allowfullscreen=””]


This is a very early Pine vehicle in which he plays a mysterious student at a parochial school. It’s trying to be a psychological thriller, but it’s a really bad movie. But Pine is a very watchable actor, doing what he can with crappy material. If you can get your hands on it, it’s worth watching a very young Chris Pine play a scary-ass psychopath. Even though the movie itself is prime RiffTrax material. But there’s also a blooper reel, which might make up for some of the badness.

Bonus: Bottle Shock and An Inconvenient Head

Bottle Shock
is another bad movie that Pine is good in, but what makes it weird is not the performance, nor the story. It’s the distractingly bad hippie wig that Pine wears throughout the movie, which is based on a true story about wine types. Is it worth a watch? Not really, unless you have, well, a case of wine.

“An Inconvenient Head” is a short film that was made before Pine scored the role of Jim Kirk. He has no lines and appears for less than a minute in this 12-minute short film about a self-conscious guy losing his hair. The “dreamboat” Pine is shown demonstrating that it doesn’t take a good head of hair to nail a lady in a public place and he gets a ton of bottles broken over his head. It’s not a great film, but it’s funny to see the Pine we all know now in something like this, knowing that he’s still willing to pop up in things here and there for the sole purpose of sh*ts and giggles. Here is Pine’s performance:

Seriously, someone needs to get Chris Pine a hosting gig on Saturday Night Live, or let him be Amy Schumer’s next love interest. Anything to see him being devastatingly funny. The handsomeness is a mere bonus.