12 Hall of Shame Moments from ‘Saturday Night Live’ Cast Members

Jimmy Fallon in blackface. Wayne and Garth mocking a 12-year-old Chelsea Clinton’s looks. Dana Carvey transforming into Camilla Parker Bowles’ tampon. Here’s the worst of the worst from Studio 8H
12 Hall of Shame Moments from ‘Saturday Night Live’ Cast Members

There’s a lot that could (and frequently does) go wrong on Saturday Night Live. Sometimes a sketch goes off the rails, sometimes a joke seems funny until it dies in front of a live audience and sometimes the topical premise of a joke has the shelf-life of an organic banana. 

It’s just the price of doing live TV for 48 seasons. But what we’re focusing on today are the times where the cast members went so above and beyond to be awful that they earned a special place in hell a spot in our Hall of Shame.

O’Callahan and Son’s Pub

SNL is no stranger to accusations of joke-stealing, but this 1995 sketch almost landed them in court. It was about a bartender who insults all of his customers and was “written” by cast member Jay Mohr. Comedian Rick Shapiro, however, claimed in court that it was lifted nearly word-for-word from his stand-up act. Mohr denied he’d plagiarized the bit and managed to keep his job until the end of season. But in 2004 Mohr not only confessed to the joke theft, but tried to rationalize it in his memoir Gasping for Airtime, a book that SNL alum Bobby Moynihan referred to as “a handbook on what NOT to do at SNL.” Shapiro settled with NBC for an undisclosed amount, and as a condition of the settlement, the sketch was removed from any future rebroadcasts (streaming or otherwise), and will likely never again see the light of day.

Canteen Boy Goes Camping

Canteen Boy was among Adam Sandler’s most popular recurring characters on SNL. Usually, these sketches were about a child-like assistant scoutmaster with a canteen around his neck getting taunted by everyone around him. But one entry from February 1994 took a turn for the creepy and kept on going. It featured Canteen Boy on a scout camping trip, with guest host Alec Baldwin playing a troop leader trying to seduce him. It was off-putting and hard to watch to begin with, but there was another layer of cringe: This was also SNL’s Valentine’s Day episode. 

NBC was flooded with complaints that the sketch made light of pedophilia. That resulted in future rebroadcasts being tagged with a disclaimer that reminded viewers that Canteen Boy (or at least Sandler) was 27. Still, we’re not sure that a “He’s a mentally challenged adult, not a child” warning was all that comforting.

Suitcase Boy

Season 11 (1985-1986) is widely regarded as one of the worst in SNL history. It was Lorne Michaels’ first year back as the show’s producer after a five-year hiatus, and it was the only time SNL had zero returning cast members. As such, experiments abounded. One such experimental misstep was an episode hosted by Cheers’ George Wendt, but in a weird twist, every sketch was also “guest directed” by Francis Ford Coppola. The episode featured this sketch, where a 20-year-old Robert Downey Jr. delivers a “confrontational monologue” while zipped up in a suitcase. There are no words to describe it.

Molly Shannon as Monica Lewinsky

The late 1990s were incredibly unkind to Monica Lewinsky, and her affair with Bill Clinton ushered in a veritable Golden Age of TV-friendly blow-job jokes. But Molly Shannon’s take on Lewinsky after her awkward interview with Barbara Walters was one of the most lazy and cruel impressions in the show’s history. The wording of the “jokes” in this Weekend Update segment was dreadful. Nor was it not much of a performance. Shannon merely exaggerated Lewinsky’s nervous giggling from the Walters interview and morphed it into full-blown psychotic laughter.

Oprah Winfrey Cold Open

Another Season 11 miss. It involved Michaels (always a de-facto cast member) visiting Winfrey in her dressing room to discuss her issues with some of the sketches they wanted her to do, including playing Aunt Jemima. During this discussion, Danitra Vance, the show’s only Black female cast member, came in to serve Michaels his coffee while dressed as Whoopi Goldberg’s character from The Color Purple. The whole thing was as tone-deaf as it sounds, especially with dialogue like this (taken from a transcript of the episode): 

Michaels: Danitra, you’re Black? 
Vance: Yes, Mr. Lorne.
Michaels: Maybe you could help me out? 
Vance: Yes, Mr. Lorne? 
Michaels: For some reason, Oprah won’t do anything I say.
Vance: Yes, Mr. Lorne?
Michaels: Danitra, what do you think I should do?

(Vance bites her lower lip and ponders for a moment.)

Vance: Beat her!

Wayne’s World Mocks Chelsea Clinton’s Looks

In this clip, you might notice an odd edit around the five-minute mark. That’s because there was a joke that made fun of Clinton’s appearance, with Wayne saying, “Adolescence has been thus far unkind.” Then Garth suggested, “She could turn into a babe-in-waiting.” Clinton was 12 at the time, and after Hillary Clinton went nuclear about the bit, Michaels decided to cut the joke from all future broadcasts.

First He Cries

In this sketch, Gilda Radner played a woman with breast cancer undergoing a mastectomy (comedy!). Yet, the main focus was placed upon Bill Murray, who played her husband and who, as a title card put it, was suffering from “the anguish of living with ‘half a woman.’” It goes on like this for over 10 minutes, with Murray trying like hell to get a laugh out of such a horrible premise. The only video online of the sketch comes courtesy of the Internet Archive (it starts at the eight-minute mark). 

Colin Quinn on St. Patrick’s Day

This one isn’t so much about what Quinn said, but how he said it. He obviously wasn’t well-versed in reading jokes off of cue cards. Norm Macdonald tried to give him a lifeline, which only threw Quinn more off-track. Attempting to ad-lib his way out of the situation didn’t help either. 

Mr. Monopoly

In 1986, Damon Wayans was sick of being on the show. He hadn’t received much airtime, and the time he did get didn’t play to his considerable strengths. And so, in an attempt to get fired, Wayans decided to ad-lib his cop character in this sketch as being flamboyantly gay. He played it straight (wordplay!) throughout dress rehearsals, but he went for it live. Wayans got his wish and was fired, although he came back to perform stand-up on the season finale and returned to host nine years later.

Stefon’s M-Word Mea Culpa

Most of the Weekend Update segments featuring Bill Hader’s Stefon are classics, but Hader and Stefon co-creator John Mulaney came under fire for their repeated use of the word “midget” during Stefon’s descriptions of New York’s hottest clubs. To address the controversy, when Hader brought the character back during a hosting stint in 2018, he also brought along his “lawyer and conceptual piss artist,” Shy, to advise him to use “little people” instead. It came across as incredibly hollow and patronizing when a simple apology would have been much more effective.

Prince Charles Phone Sex Talk

When a transcript of a phone conversation between then-Prince, now-King Charles and his then-mistress, now-wife Camilla Bowles leaked to the press, and the world found out that Charles wished he could be reincarnated as her knickers, maybe even her tampon, SNL took that last part and ran like hell with it — and as you can probably guess by now, not in a good way. Dana Carvey as Charles began the sketch by addressing the tampon controversy, and he quickly (and cringely) drove the whole thing into the ground, actually turning himself into a tampon at the sketch’s conclusion.

Jimmy Fallon in Blackface

Yet another sketch that’s been taken out of circulation. Back in 2000, Jimmy Fallon played Chris Rock in a Live with Regis and Kelly parody — in full blackface. We could go around and around in circles arguing how it wasn’t done with malice, how Fallon and Rock remain good friends and how Fallon apologized years later, but it doesn’t change the fact that it didn’t need to happen. There were just so many opportunities — during the pitch, the writing process, rehearsal, etc. — for someone, anyone to step in and say, “Hey, could we not?”

Come to think of it, those words hold true for everything on this list. 

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