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Will Ferrell might be one of the funniest men to ever work in showbusiness. He’s starred or appeared in more classic comedies than most actors could dream of, almost all of which contain at least one scene that can still put you on the floor in stitches.

One film of the early 2000s, Old School, has a particularly memorable example of this. However, the story behind it might be even funnier than the scene itself.

‘Old School’ saw Will Ferrell bare it all several times

'TRL' hosts the stars of 'Old School,' Vince Vaughn, Will Ferrell, and Luke Wilson, in 2003
Vince Vaughn, Will Ferrell, and Luke Wilson on TRL in 2003 | Theo Wargo/WireImage

Old School follows a trio of washed-up 30-somethings played by Luke Wilson, Vince Vaughn, and Ferrell himself. Throughout the Todd Phillips-directed film, the trio seeks to relive their glory days by starting up their own fraternity. Hijinks ensue as they so often do in these situations.

The men’s antics jeopardize the status of their fraternity and personal relationships. Ferrell, who plays the character of Frank “The Tank” Ricard, steals the show in almost any scene. Surprisingly enough, one of his most memorable scenes comes fairly early in the movie.

During a massive housewarming party, Frank ends up getting extremely drunk and stripping naked before running through the streets. It was a funny scene to be sure, though maybe a bit too close to reality for Ferrell. He had to film the scene over 100 times to get it right.

Ferrell’s awkward position during the extremely long shoot

During an episode of the torturous web series Hot Ones, Ferrell reminisced about Old School through spice-induced tears. According to Elf actor, the streaking scene wasn’t supposed to take so long to get right. However, extenuating circumstances caused the shoot to go extra long.

Of all people, Snoop Dogg was at least partially to blame. He always took a while to leave his trailer on account of all the fun (weed and video games) in there. Frankly, he never seemed to care much about the movie itself, according to Ferrell. He only accepted the cameo role due to his interest in playing Huggy Bear Brown in the then-upcoming Starsky & Hutch film, helmed by Old School‘s director.

Because of Snoop’s slow start, Ferrell resorted to drinking in between takes. Getting drunker throughout the night, he was sloshed by the time things ended and he ran through the streets naked. They needed around 110 takes to get it right. Ferrell also revealed on That Scene With Dan Patrick that at least some of the people he passed on his way through the quad weren’t actors or crew, but real Pasadena residents.

Will Ferrell has a history of stripping down for films

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Old School isn’t the only movie Ferrell’s taken his clothes off for. In Talladega Nights, Ferrell’s character is engulfed in a raging invisible fire that forces him out of his clothes as he desperately tries to put it out. Semi-Pro sees the actor strip down to his tube socks and headband to advertise his basketball team, the Flint Tropics. 

While it’s not full nudity, Step Brothers saw him infamously whip something out to rub on a drum set. Ferrell even kept the prosthetic they made for that scene. In Anchorman, he showed plenty of skin particularly at the pool party near the start of the comedy.