The 10 Raciest ‘Saturday Night Live’ Moments of All Time

From Dick in a Box to Lindsay Lohan's busty Hermione, look back at the SNL moments that almost gave the FCC a heart attack.

– Additional research by Jim Miller (@jimmiller)

Saturday Night Live is celebrating its 40th anniversary on February 15, and VH1 Classic is throwing the marathon of a lifetime. Beginning tomorrow, the network will air “SNL Rewind: 2015- 1975 Mega Marathon,” which will feature 433 hours of episodes, over the course of 19 days (Jan. 28-Feb. 15). Basically, if you’re an SNL stan, clear your schedule, because this is your wet dream come true.

But now shouldn’t be the only time SNL’s gotten you excited. Forty years means hundreds of episodes worth of the sexiest, or most uncomfortable (depending on your disposition), moments that live television has to offer. Now, kick off your nostalgia trip and get your blood racing with the 10 raciest moments in Saturday Night Live history.

  1. Jane Curtin Flashes the Camera on Weekend Update (Season 2, Episode 13)

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    As the first female Weekend Update host, Jane Curtin took a moment to address her haters. Their biggest critique? She wasn’t Chevy Chase, the man she replaced. Starting her segment, Curtin read aloud a fan letter, one out of dozens apparently, blaming her for SNL’s decline and claiming to miss Chase’s “sexiness.” Like a big middle finger to Chevy stans, Curtin ripped her shirt wide open on live television, flashing her lacy bra. Sexy enough for you, America?

  2. Dan Aykroyd Propositions Margot Kidder as Male Prostitute, Fred Garvin (Season 4, Episode 15)

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    Here, Dan Aykroyd propositions host Margot Kidder, whose character is visited by a male strumpet in her hotel room as a gift for doing business in the city. Ripe with sexual innuendos, Garvin says he’s there to “roger” her “roundly” and flashes his “backseat driver’s license.” She refuses at first, but his persistence eventually works. Just as he climbs into bed with her, sans pants, his pimp Slick (Garrett Morris) swaggers through the door and climbs into bed with the clearly unnerved Kidder. Just think of all the thinkpieces this sketch would’ve inspired today.

  3. The Word “Penis” Is Said 43 Times in Matthew Broderick’s “Nude Beach” Sketch (Season 14, Episode 2)

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    Hearing the word “penis” uttered 43 times was not a common thing in 1988, which is why this sketch (written by Conan O’Brien) was struck down twice before it made it on air. About a group of men commenting on each other’s genitalia at a nude beach, the sketch was originally written for Carl Weathers’ episode, only to be moved to Tom Hanks’ episode later in the season. This time, the sketch made it all the way to dress rehearsal, but was cut from the live show. It finally aired during the Matthew Broderick episode, which allegedly received thousands of letters of complaints.

  4. Patrick Swayze and Chris Farley Compete for a Spot on Chippendales (Season 16, Episode 4)

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    We’d like to think this sketch set the stage for Magic Mike, and inspired a young Channing Tatum to thrust his way into our hearts. Starring Patrick Swayze and Chris Farley as aspiring strippers Adrien and Barney, respectively, the sketch pits the two against each other in a striptease dance battle for the last spot on the all-male dance troupe. As judges Kevin Nealon, Mike Myers, and Jan Hooks look on, Swayze sways his rock-hard abs and flaps his junk, while Farley’s belly fat takes on a life of its own. Swayze’s appeal is obvious, but surely there were some chubby chasers out there who had to fan themselves after this aired.

  5. Madonna Seduces Wayne and Garth on “Wayne’s World” (Season 16, Episode 19)

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    WAYNE'S WORLD SKETCH 1990 featuring Madonna by kervez As a response to the backlash against her 1990 music video for “Justify My Love,” which depicted the pop queen being seduced into a threesome with a man and a woman, and promo for her new documentary Truth or Dare, Madonna made a surprise appearance in the Delta Burke-hosted episode six months later. In a Wayne’s World sketch, the singer shows up in Wayne’s (Mike Myers) black-and-white dream. Here, she’s sprawled out on a bed and asks Wayne to play a game of Truth or Dare with her. The pair end up making out, and as they do, Garth (Dana Carvey) is seen on TV in the background with two women in fetish-wear. Remember, before Lady Gaga could even think of being birthed from an egg on live television, Madonna was the queen of shock.

  6. Cuba Gooding Jr. Flashes Monica Lewinsky (Season 24, Episode 18)

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    There are many moments in SNL history that are far too scandalous to ever make it to air. For the most part fans never hear of them, but Cuba Gooding Jr.’s hosting gig is an exception. In his episode, he was to appear in a sketch with Mango (Chris Kattan), the exotic dancer who was cursed with making everyone, man or woman, fall in love with him.

    During the read-throughs, the special guest Monica Lewinsky was to be revealed, shockingly, to be Mango’s wife and mother of his children. It was a hilarious sketch that Gooding went all in for, and when the script called for him to lift up his shirt, he also dropped his pants and placed his butt mere inches from Monica’s face. She responded in the classiest way possible, “That’s the most action I’ve gotten in months,” and let Molly Shannon take over the role of Mango’s wife when it finally aired. While the ass-flashing isn’t online, you can still relive Gooding Jr.’s episode with something a bit tamer: his opening monologue.

  7. Canteen Boy and the Scoutmaster Make Everyone Uncomfortable (Season 19, Episode 13)

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    Obviously not a sexy moment, but Canteen Boy (Adam Sandler) and his Scoutmaster (Alec Baldwin) is undeniably racy. While Canteen Boy is a full grown man-child, who still attends troop meetings, the Scoutmaster is a pervert who acknowledges, “[his] beard may be scratchy, Canteen Boy, but it gives good backrubs.” The infamous sketch drew a lot of criticism to NBC and SNL, when viewers found it in poor taste, homophobic, and drawing upon imagery of pedophilia. On reruns, there is a disclaimer that states Canteen Boy is actually 27, to clear up any confusion.

  8. Lindsay Lohan’s Hermione Has a Growth Spurt (Season 29, Episode 18)

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    During the same time people started to notice that Lindsay Lohan wasn’t the freckled-face twin in the Parent Trap anymore, she hosted SNL. This lead to, of course, her playing Hermione after a long summer, and a huge growth spurt. Ron (Seth Meyers) and Harry (Rachel Dratch) aren’t the only ones who notice, Fred (Chris Parnell) and George (Jimmy Fallon) do, too, and what follows is an uncomfortable sketch of older teachers, Hagrid (Horatio Sanz) and Snape (Will Forte) ogling Lohan’s rack just as the audience gets a clear view of her cleavage.

  9. The “Dick in a Box” Digital Short Pleasantly Surprises (Season 32, Episode 9)

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    If SNL rumors are to be believed, than “Dick in a Box” was almost cut from the show. The Lonely Island members who worked on it thought it was a stupid joke and not going to go anywhere. Justin Timberlake, however, believed in the little dick in a box that could. (That sentence came out wrong. Let’s move on.) The song was such a hit that it won the Creative Arts Emmy for Outstanding Original Music and Lyrics. Not many songs about a gentleman’s surprise package can boast that.

  10. The “Dongs All Over the World” Music Video Packs A Feminist Punch (Season 39, Episode 17)

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    It’s about time that women grabbed the world by the dong and took control. The International Nasty Girls, played by Anna Kendrick, Sasheer Zamata, Aidy Bryant, Kate McKinnon, and Cecily Strong, with some vocal help from Icona Pop, proved how sick they were of the sexist ideology that men can have hoes in different area codes, but women could not. Their solution was simple: forget that dick in a box, hop on a plane and discover all the dongs the world has to offer.

Tara Aquino is an entertainment writer based out of L.A. She likes people, places, and things.