Brad Pitt's Hair Through the Years

1988: The Boy

Look at him! Fresh faced. Mother approved. That one dangly wisp in the front represents every guy who has ever been cooler than you, yet manages to still be likable. This is the laissez-faire hairstyle of teen boys everywhere.

1989: The Concerned Boy

Everything from above, but make him complex. This is one of the earliest signs that Brad Pitt and Brad Pitt's hair would have two separate, yet congruous careers.

1991: A Hand Runs Through it

Here, the boy is evolving into a man. The blonde hair has been chopped into something resembling a more uniform cut, but the face and demeanor maintain their youth. Fun fact: This is also the year that Brad Pitt hooked up with Geena Davis in a hotel before stealing her money!

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1992: The Experiment

There is a point in every young man's life (perhaps you're going through it right now), when he just lets all the hair grow. This is what seems to be going on here, and it's a weird dichotomy between an older, masculine bottom half of the face and a bizarrely boyish long cut up top.

1993: Long Locks

It really is a shame that The OC wasn't filmed in the early '90s.

1994: The Pain of Cobain

With nary a bottle of conditioner in sight, this Interview with a Vampire situation is a real misstep. And, just being frank, you never want to hear the words "but your roots," but... his roots. Nevertheless, this hairstyle smacks of a very particular era, and for that, it gets a pass.

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1995: Short Spikes

For some reason, this hairstyle just encapsulates an entire era. Pitt was doing it early, but this short, messy, spiked updo stays popular well through the early 2000s.

1996: The Uncle Brad

The tendrils. The goatee. The nondescript length of hair in the front and back. This man has annually offered me an L&M cigarette while leaning against my parents outdoor freezer since I was nine years old. He talks at length about the Plymouth Duster I. He makes sure you don't want that cigarette before going back in for Thanksgiving dinner.

1997: Property of Gwyneth

To defend Brad in this photo, it should be noted that he's dating Gwyneth Paltrow at this point in life, which should explain everything. But the blonde exo-strands that seem to be shooting off his head are a bit bizarre. For those who remember the turn of the millennium, there was a lot of anxiety about whether computers would fail. We had bigger fish to fry than a questionable haircut.

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1999: Live Fast, Die Young

One of my favorite things about Brad Pitt is his ability to somehow look younger years after a previous era. In this photo, this hairstyle is the manifestation of what he looked like while driving the Plymouth Duster I discussed in 1996.

2000: Wet and Wild

Ah, yes, the Snatch era. A bit oilier than I'd like, Pitt is somewhere between Ellen Degeneres coming out on national television and Kurt Cobain. The length suits him surprisingly well... it's just that strange wet look that never seems to land correctly.

2001: The Movie Star

This is a classic Pitt look. The short hair! The illusion of a Widow's Peak! This man somehow looks aspirational and rich, while also appearing approachable. Arguably, this is also the beginning of Pitt's proper movie-star era.

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2002: Haley Joel Osment

There is a 45 percent chance this is Haley Joel Osment.

2003: Soft Waves

I can't shake the feeling that this haircut is somehow inspired by Hillary Duff. Nonetheless, this long hairstyle is working. Ultimately, Pitt almost always looks better with a shaved face, which allows the flowing blonde locks to do the heavy lifting. This is what good, washed hair looks like.

2004: The Buzz

Few men can pull off a buzzcut without looking like a white nationalist. Sorry, that's just the rules. However, Pitt makes it work. There are few shocks like fully cutting your hair down within an inch of your head, though, so to avoid that "Not Mein Problem" aesthetic, don't go too short and beware majorly if you're a light blonde.

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2006: The OG Gen Z

There is this thing that the upcoming generation of young men do with their hair where it seems to leave the front of their scalp and just float in space. It's hard to explain, but when searching for past Pitt images, this one jumped out because, naturally, Pitt managed to create this vibe way before some of these kids were out of diapers. The way some of the follicles just jut out into the ether without so much as a care? Beautiful.

2007: Old Hollywood

Hardly his most popular look, I'd like to make the argument that his is what Pitt does best. Movie stars are a dying breed, and Brad Pitt is probably one of the last of the greats. Here, all he's done is slicked his hair back with a part, but it looks coiffed. It looks smart. It looks timeless. Not pictured: Angelina Jolie looking equally glamorous in Old Hollywood-style dress and hair.

2008: Not Today

It's the goatee. I swear to God it devalues his hair every time. This is another variation of the Gen Z, but the hair just happened to not have the energy today.

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2009: The Croque Monsieur

At the time he played Aldo Raine in Inglourious Basterds, Pitt reimagined that Old Hollywood look, threw a scarf on it, and grew out the bravest little mustache. It works. While some prefer the youth of Pitt, a couple of forehead wrinkles and a sensible haircut that has the potential to show off both volume and class is where he thrives. Note: the dangling tendril that made him cool in 1988 remains, albeit more subtle. You beautiful bastard.

2010: The Aviator

No, I'm not talking just about the glasses. Something about this cut screams Tom Cruise vibes. Even with the wild missteps of the past, this is the first cut that makes Pitt seem a little...old. Even for the timeframe. Fortunately, this is not a look that holds.

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