Alright, pretend I had this idea when Benjamin Button first was being released a few months ago and it will seem much more timely. But it just hit me now, so we’re going to go through with it anyways.

What I’ve collected are stills from almost all of Pitt’s major roles over his long career, and compiled them in reverse order below, starting with Inglorious Basterds and ending with 21 Jump Street. See the Button reverse aging connection now? Yeah, whatever, I’m clever.

I’d like to make this a running series every so often, (with other actors, not just Brad Pitt over and over) so let the inaugural run begin:

Inglorious Basterds (2009) - Lt. Aldo Raine

Pitt’s latest role puts him in a WWII movie, somewhere we’ve never seen him, but it’s under the reign of director/psychopath Quentin Tarantino, so it should be anything but ordinary. So far, all we know is Lt. Raines got his throat cut once, and wants his SCALPS!
The Curious Case of Benjamin Button (2008) - Benjamin Button

The inspiration for this post, Pitt’s role as Button earned him an Oscar nom, but unfortunately in a year of a lot of worthy contenders. None of whom were Sean Penn.

Burn After Reading (2008) - Chad Feldheimer

I didn’t like this movie at all, but Pitt was by far the highlight as goofy gym rat Chad. His dancing in the trailer alone made eighty percent of the audience show up at all.

The Assassination of Jesse James by the Coward Robert Ford (2007) - Jesse James

This picture perfectly sums up this movie, Jesse James, standing in a field, not shooting anyone. Seriously, about 70% of the movie was some variant of this shot, and Pitt’s acceptable acting couldn’t save it.

Babel (2006) - Richard Jones

Another movie with some awards hype, but it ultimately it amounted to nothing. I saw it, but immediately forgot everything that happened in it. Brad Pitt is upset because…he couldn’t get through to vote for Taylor Hicks? I don’t know.

Mr. and Mrs. Smith (2005) - John Smith

The movie that ruined a marriage, Mr. and Mrs. Smith wasn’t even particularly good as a romantic comedy or an action movie. But it was mildly entertaining to watch the two most beautiful people on earth try to kill each other.

Troy (2004) - Achilles

Brad Pitt put on 10,000 lbs of muscle for this role, and although his fight scenes were amazing, someone should have told him that Greeks don’t have British accents. And if they did they would consistently have them for the entire movie.

Ocean’s 11 (2001) - Rusty Ryan

Here Pitt was only part of a massive A-list ensemble, in a movie that spawned both a good and bad sequel. Have we seen the last of the Ocean series? I kind of doubt it.

Friends (2001) - Richard Colbert

Back in the good old days when it was still “Brad and Jen,” (we didn’t have a cute nickname for them), Pitt guest starred on an episode of friends, where he spent the entire time giving Rachel hell. Probably one of my favorites of the series.

Spy Game (2001) - Tom Bishop

Can you really make an entire movie to demonstrate the “passing of the torch” from one actor to another? If so, that movie is Spy Game, where Robert Redford officially anoints Pitt as the charming young actor of our generation. I remember zero things that happened in this movie.

Snatch (2000) - Mickey O’Neil

One of my favorite Pitt performances, he took on the role of a gibberish-talking gypsy boxer that even subtitles couldn’t save. I’d love to see this character come back in another Guy Ritchie film. Don’t act like it’s not perfectly plausible.

Fight Club (1999) - Tyler Durden

In my opinion (and I’m guessing many others’), Pitt’s best role. Tyler Durden was manic, psychotic, and probably one of the greatest film characters of all time. I think there’s been a poll to prove that somewhere.

Meet Joe Black (1998) - Joe Black

Most people hated this three hour epic, but I actually enjoyed it. Sure, the entire movie was people walking around and talking to each other while wearing suits, but it’s Brad Pitt as Death! Come on!

Seven Years in Tibet (1997) - Heinrich Harrer

Ugh. This was awful. And look at the picture. Do you think Sasha Baron Cohen might have gotten some inspiration for Bruno there? This movie meanders aimlessly for hours and Pitt has a pretty horrendous accent. Avoid at all costs.

Twelve Monkeys (1995) - Jeffrey Goines

Pre-Durden, this was Pitt’s zaniest role to date. I’m not a huge fan of Twelve Monkeys like most other people, but he was certainly pretty excellent as psychotic activist leader Jeffry.

Se7en (1995) - Detective David Mills

“What’s in the box? What’s in the box?” Don’t get me wrong, Se7en is awesome, but I’m not sure how much Pitt actually brought to his role, (aside from aforementioned box scene). I feel his character could have been anyone and the movie would have still been incredible due to Freeman, Spacey and Fincher alone.

Legends of the Fall (1994) - Tristan Ludlow

Brad Pitt being charming on a ranch? I never actually saw this one. Was it good?

Interview with the Vampire (1994) - Louis de Pointe du Lac

Totally not gay. That is all.

True Romance (1993) - Floyd

I’m ashamed to admit I’ve never seen True Romance, but it’s clear it’s not exactly one of Pitt’s hearthrob roles.

A River Runs Through It (1992) - Paul Maclean

How is this different than Legends of the Fall? I see the same hat. Damn, he looks young though.

Thelma & Louise (1991) - J.D.

Pitt’s “breakthrough role” as they call it, he played seductive con man J.D. in the cult classic, and began his rise to stardom shortly after.

Growing Pains (1989) - Jeff

Now we’re going way back to his early guest-spot TV days. I don’t remember this episode, but its interesting to remember that fellow A-lister Leonardo DiCaprio started out on this show.

21 Jump Street (1988) - Peter

That’s a crazy picture huh? Young Johnny Depp got his start on 21 Jump Street, Pitt also briefly appeared on the show. This picture makes me think that Bill and Ted’s Excellent Adventure should have been re-cast.

Another World (1987) - Chris

The absolute earliest shot I could find of Pitt onscreen. If he was in some Gerber’s commerical as a kid, let me know.

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