14 Heartthrobs Who Went Left

Your '90s poster boys are looking a little...rough.

The late ’90s and early ’00s were weird times for all of us. You probably chewed way too much bubblegum, daydreamed of your first Nokia phone, and had posters of Joey Fatone hanging all over your lime green-colored room. But even weirder is what some of those poster boys look like today. Questionable hair choices and skipping the gym have made some of your former crushes look a little rough. Proceed at your own risk.

  • 1 Brad Pitt
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    This photo was taken in 2013, proof that age isn’t what makes someone go left. [/item
  • 2 Brad Pitt
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    It’s not grooming yourself. We’re 99 percent sure Pitt’s breakfast has set up camp in that disheveled beard. [/item
  • 3 Josh Hartnett
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    So dreamy, right? [/item
  • 4 Josh Hartnett
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    So creepy, right? (The word grease comes to mind.) [/item
  • 5 Luis Miguel
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    Swoon. [/item
  • 6 Luis Miguel
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    Swerve. [/item
  • 7 Haley Joel Osment
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    Serving up pure prep school cutie realness. [/item
  • 8 Haley Josel Osment
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    Now, HJO looks like a frat boy about three beers too deep. (And three years past his expected graduation date.) [/item
  • 9 Shia LaBeouf
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    In 2011, LaBeouf had the smolder to make you instantly pregnant. [/item
  • 10 Shia LaBeouf
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    Now, his rattail will make you instantly squeamish. [/item
  • 11 Johnny Depp
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    Depp’s grungy look was totally sexy in 2005. [/item
  • 12 Johnny Depp
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    In 2015, he just looks slightly tipsy. [/item
  • 13 Gerardo/Rico Sauve
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    Basking in his hotness. [/item
  • 14 Gerardo/Rico Sauve
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    Basking in his creepiness. [/item
  • 15 Mekhi Phifer
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    So beautiful. [/item
  • 16 Mekhi Phifer
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    So…something. [/item
  • 17 Diego Luna
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    It’s like he’s staring into our souls, and we’re cool with it. [/item
  • 18 Diego Luna
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    Alright, it’s time to stop looking. [/item
  • 19 Jesse McCartney
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    We don’t speak Spanish, Japanese or French either, McCartney. But we do speak hot, and that’s what you were in 2010. [/item
  • 20 Jesse McCartney
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    We don’t compute with this. [/item
  • 21 Leonardo DiCaprio
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    Millennial Leo needs no words. [/item
  • 22 Leonardo DiCaprio
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    Today, he also needs no words. But for the exact opposite reason. [/item
  • 23 Joey Fatone
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    While he wasn’t the most sought-after *NSYNCer, Fatone was still in the band — which means there were at least 50,000 tweens who idolized him. [/item
  • 24 Joey Fatone
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    Now, he looks like Guy Fieri’s brother. [/item
  • 25 D’angelo
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    Biceps for days. [/item
  • 26 D’angelo
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    *Listens for the swooning females* *Realizes there are no more swooning females* *Walks off stage* [/item
  • 27 Matthew Underwood
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    Admit it: 13-year-old you thought Logan from Zoey 101 was the beez-neez. [/item
  • 28 Matthew Underwood
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    While he’s still cute, homeboy just went straight up left. (Yes, that’s a mugshot you’re looking at, circa 2012.) [/item