We've had our eyes on Chris Pine since he blew us away as Captain Kirk in 2009's 'Star Trek,' but in today's Way Back When we'll take a look at one of Hollywood's handsome leading men before he was a big star.


Chris Pine's very first role was in a 2003 episode of the long-running TV series 'E.R.' Pine plays a patient at the hospital who has apparently been drunk for five days. Watch Pine in the clip below (he shows up somewhere around the :35 mark) as he slurs his words and gets really stoked about having an IV in his arm.

'CSI: Miami'

What the hell is going on with this moppy hair and that tacky lip ring, C-Pine? In this episode of 'CSI: Miami,' Pine tries and almost succeeds in out-acting David Caruso as a guy with a pretty sinister sexual hang-up. As if looking at that lip ring wasn't enough to make you drop dead...

'The Princess Diaries 2: Royal Engagement'

Now this is definitely a step up from that face-metal business: Pine starred alongside Anne Hathaway in 'The Princess Diaries 2,' in which the princess is being offered up in an arranged marriage, but she's really into Chris Pine. And after watching this fountain scene, we can see how that works:


We have a confession to make about this really, really long trailer for 'Confession': it looks ridiculous. Pine stars as a student at a Catholic school who gets busted for selling porn, pills and booze to his fellow classmates, and then the kid that snitched on him winds up dead, and maybe Pine did it or maybe this priest guy did it. And oh hey look, it's the dad from 'Happy Days.'

'Six Feet Under' (Language NSFW)

On the HBO drama series 'Six Feet Under,' Pine guest stars as a young version of a man who died. We're not sure what's worse: his bad hair and jean jacket combo here, or the bad hair and lip ring combo from that 'CSI: Miami' clip. You be the judge. But what we are sure of is that Pine definitely improved as an actor since that 'CSI' appearance:

'Surrender, Dorothy'

In 2006, Pine starred with Diane Keaton and Tom Everett-Scott in the made-for-TV movie 'Surrender, Dorothy,' about a woman whose teen daughter passes away suddenly, leading her to the summer house where they used to spend their vacations together. Pine plays a friend of the daughter who's like, one box of wine away from seducing Diane Keaton -- you know, if that's what he's into.

'Just My Luck'

Oh, oh there are so many things going on in this trailer. Chris Pine was in a movie with Lindsay Lohan back when we still had hopes for her future, people using the phrase "my bad," and Sarah Jessica Parker name-dropping when 'Sex and the City' was still a huge deal. Just your typical mediocre post-'90s rom-com: