6 Hilariously Awkward Old Photos Of Famous People

If you’re anything like us, you live under constant terror that one day, the entire world will see that photo of you. You know, the one with the awkward hairdo, or the awkward outfit, or the awkward … you. The good news is that “the entire world” will probably never see that, because you’re not famous and who the hell cares? The even better news: We’ve dug up a generous cache of embarrassing old photos of legitimate celebrities, so let’s make fun of them, shall we?

6

Here’s Christoph Waltz Singing In Rainbow Overalls

Contrary to popular belief, Christoph Waltz was not magicked into existence by Quentin Tarantino in 2008. Prior to playing the bone-chillingly pleasant Nazi colonel in Inglourious Basterds, Waltz was just another Austrian actor trying to make it big. In 1976, he joined the cast of a children’s show called Am Dam Des, which required him to dress like this:

ORF StudiosYes, they made him wear that red shirt. The rest is normal ’70s fashion.

That’s a 21-year-old Waltz looking like he’s about to run a charity 5k for people who have chromatic coordination disorder. Here’s a video of him singing that we can’t embed in this article because the sheer sensuality would destroy our servers, so here’s a short sample:

ORF StudiosThis is from sometime in the late ’70s, but it’s impossible to pinpoint the exact year.

If you watch the clip with the auto-translated subtitles, you’ll discover that Waltz is playing the personification of 1977, and he sings a song about the ceaseless march of time, with a friendly reminder that death is always around the corner. We assume that the target audience is too young to have an existential crisis from this, although it’s also entirely possible that German and Austrian children are expected to have come to terms with their own mortality by age five.

5

N.W.A’s Original Look Was Less Gangsta, So 1980s

When you pioneer an entire genre of music and release one of the greatest rap albums of all time, it’s important to cultivate a certain image. The members of N.W.A did that so well that if you try to picture them in your mind’s eye right now, they’ll probably be wearing black jackets and looking at you like you farted near their moms. They won’t be, say, chilling by a wall in pastel-colored clothes. Like these chumps:

Ruthless recordsThe world’s shadiest Jackson 5 cover act.

As you’ve probably guessed, that’s seriously N.W.A before they got the “A” part right. From left to right, we have Ice Cube, Eazy-E, Dre, and Arabian Prince (the Pete Best of the group, leaving right as they made it big). Here’s another early photo for which they apparently decided their aesthetic was “on their way to pick up the kids from Little League practice.”

Ruthless recordsTaken moments before Coach Eazy was ejected for threatening to cap an ump on a strike call.

We’ve talked before about Dr. Dre’s unfortunate experimentation with medical props and fancy getups, but luckily, they got things figured out in time for their first album, or it would have been more like Straight Outta The Hamptons.

Ruthless recordsCant have street cred without a nice knit cardigan.

4

Tina Fey Put Her Awkward Yearbook Photo In 30 Rock

The world has yet to produce a non-cringeworthy yearbook photo, and this goes double for you if you’re proud of yours. Odds are, though, that Tina Fey has you beat:

Upper Darby School DistrictOh no.

Before she became the master and commander of prime-time comedy, Fey was nothing but a dorky high-schooler like the rest of us, taking a yearbook photo with an ill-advised prop and terrible background contrast. But instead of casting all her yearbooks into the fires of Mt. Doom like everyone else, she embraced the awkwardness and used the picture for a 30 Rock gag (the shot below is followed by “I gotta get a real headshot”):

NBCUniversal Television“Wow! Mike From Stranger Things Is All Grown Up”

The internet has been quite adept at digging up photos of young Fey, like this one of her and her brother meeting (future 30 Rock guest star) Elvis Costello while wearing his face on their bodies:

Tina FeyOr at least some guy in shades who didn’t have the heart to say no.

3

Here’s Pablo Escobar Taking His Kids To Disney World

Pablo Escobar was one of the most violent drug lords in history, responsible for untold thousands of murders and smuggling 15 tons of cocaine per day into the U.S. at his peak, raking in $26 billion a year. He was also, however, the father of two kids. And as a family man with deep pockets, you bet your ass he had to take those kids to Disney World at one point.

Escobar FamilyAbove: Escobar silently contemplating the Pluto/Goofy paradox.

In 1981, Escobar was rolling in dough but still hadn’t been publicly outed as a drug kingpin, so he could travel freely under his own name. The most dangerous man on Earth used that freedom to take his family to the happiest place on Earth, hauling the entire Escobar clan to Walt Disney World in Florida. And despite looking thoroughly pissed in the above picture, Escobar’s son claims that his dad was like a little kid for the entire trip, dropping an absurd amount of cash to hire a personal guide and buying several suitcases’ worth of Disney souvenirs. Escobar was also reportedly scared of roller coasters, but rode them to satisfy his son. We invite you amuse yourself for a moment with the image of a ruthless drug tycoon adorned in Mickey ears being reluctantly led into the line for Space Mountain.

Escobar FamilyThis was the most tense and action-packed episode of Narcos.

Escobar was so impressed with the park that he used it as inspiration for his own compound, which incorporated dinosaur statues, a go-kart track, a zoo, and ecosystem-destroying hippos (not in tutus, unfortunately). The compound was seized by the Colombian government after Escobar’s death and today is a public zoo and museum, colloquially called “Pablo World.” So if your kids are bugging you and you can’t afford a Disney trip, keep that in mind.

2

Brad Pitt And Jason Priestley Living Like Joey And Chandler, Watching The Big Game

Did you know that Al Gore was college roommates with Tommy Lee Jones? Or that Cameron Diaz’s high school weed dealer was Snoop Dogg? It’s hard to say what is so appealing about finding out that random famous people hung out before they got famous, but here’s a couple more for the useless trivia part of your brain.

Via Digitaltrends.comAh, the universal “Check it out: a beer” roommate gesture.

With bare walls, dirty dishes on the floor, and the use of lawn furniture and office chairs in lieu of actual seating, this picture would be a strong nominee for the international standard of a “dude apartment,” but this is in fact a group of friends watching the Super Bowl. Sitting in the foreground in the white shirt is Jason Priestley (sex god of the ’90s), and in the back with the beer bottle dick is Brad Pitt (sex god of eternity), who were roommates during their early days in LA. Priestley would hit superstardom first by landing the leading role in Beverly Hills 90210, but it’s safe to say that Pitt has caught up to him by now.

And in case you were still thinking that this was anything other than a bachelor pad, Priestley revealed that he and Pitt would have contests to see who could go the longest without showering and shaving. He also remarked that Pitt always won, since Priestly would have to shower and shave to go on auditions. We’re gonna guess he still auditions more than Pitt today.

1

Stephen King Was Your University’s Hairy Weirdo

Believe it or not, there was a time when 30 percent of all media wasn’t based on Stephen King stories. Back in the early ’70s, King, only a few years out of college, was releasing his first novel — a thoughtful, gym-warming story called Carrie. His alma mater, the University of Maine, was excited to announce that one of their own was now an author, so they published a brief piece about it in the school newspaper, where King had once been a columnist. Realizing that most people probably wouldn’t know him by name, they decided to include a helpful file photo of him:

The Maine Campus“Oh! That guy. Yeah. *shudders* Yeah.”

Aaaand there’s King looking like he just burst through your bathroom door with an ax. The article decides to ignore the 800-pound unibrowed elephant in the room, instead relating the details of his book deal. It’s almost as if someone scary had been staring at them as they wrote this and they didn’t want to piss him off.

When he’s not trying to be best friends with Tina Fey, Chris can be found on Twitter.

We’d like to take this opportunity to remind you that Carrie is also a musical and it’s great.

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Marissa Safont6 Hilariously Awkward Old Photos Of Famous People

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