Saturday Night Live's SNL50 special looked back on the iconic sketch comedy show's most popular moments, but the broadcast also highlighted some of the most poorly aged bits and guest appearances.
A clip packaged air toward the end of the 50th anniversary special included clip a clip of Sean 'Diddy' Combs appearing on SNL years earlier, which was shocking in hindsight as the rapper sits in jail awaiting his trial on sex trafficking and racketeering charges, all of which he has vehemently denied.
The 55-year-old rap mogul even mentioned the disgraced singer and convicted sex trafficker R. Kelly in his sketch, which allowed the show to cut to a 2013 episode in which R. Kelly joined Lady Gaga to perform a musical number.
Tom Hanks used all the gravitas at his disposal to introduce the segment, which initially seemed like it would be an in memoriam tribute.
'As we celebrate the achievements of the past 50 years, we must also take a moment to honor those who we've lost, countless members of the SNL family, taken from us too soon,' he said somberly.
'I'm speaking, of course, about SNL characters and sketches that have aged horribly. But, even though these characters, accents and, let's just call them... ethnic wigs, were unquestionably in poor taste, you all laughed at them.
Saturday Night Live's SNL50 special looked back on some of its most awkward and offensive sketches over the years. Among the cringiest segments was an appearance by Diddy
The 55-year-old rap mogul even mentioned the disgraced singer and convicted sex trafficker R. Kelly in his sketch, which allowed the show to cut to a 2013 episode in which R. Kelly joined Lady Gaga to perform a musical number
Tom Hanks used all the gravitas at his disposal to introduce a segment that initially seemed like it would be an in memoriam tribute
'So if anyone should be canceled, shouldn't it be you, the audience?' he continued. 'Something to think about. Anyway, we now present to you this in memoriam.'
Diddy's appearance came under the 'problematic guests' heading and originated from a 2010 episode in which Robert De Niro — who was a guest on SNL50 — had hosted.
The skit in question, which featured De Niro cross dressing to play the mother of Andy Samberg's character, showed Diddy as he tried to record in the studio before finding himself enamored of De Niro's character, culminating with the Raging Bull star grinding on Diddy.
The clip package segued with Diddy's hilariously unfortunate lines: 'Don't judge a book by it's cover. My man is like R. Kelly —'
Then the show cut to R. Kelly grinning next to Lady Gaga at the end of a 2013 episode.
They weren't even the only problematic guests, as John Mulaney had joked earlier that SNL had had 'two murderers' host, which apparently referred to O.J. Simpson and Robert Blake.
Tom was skewering himself, as he was featured among the offensive 'ethnic stereotypes.'
Rob Schneider made an appearance as a Mexican with a stereotypical mustache, sombrero and poncho as he spoke about NAFTA, while Dana Carvey played an oversexed Italian waiter.
'Even though these characters, accents and, let's just call them... ethnic wigs, were unquestionably in poor taste, you all laughed at them. So if anyone should be canceled, shouldn't it be you, the audience?'
Diddy's appearance came under the 'problematic guests' heading and originated from a 2010 episode in which Robert De Niro — who was a guest on SNL50 — had hosted
The skit, which featured De Niro cross dressing to play the mother of Andy Samberg's character, showed Diddy as he tried to record in the studio before finding himself enamored of De Niro's character, culminating with the Raging Bull star grinding on Diddy
The clip package segued with Diddy's hilariously unfortunate lines: 'Don't judge a book by it's cover. My man is like R. Kelly —' Then the show cut to R. Kelly grinning next to Lady Gaga at the end of a 2013 episode in which the two performed a song together
They weren't even the only problematic guests, as John Mulaney had joked earlier that SNL had had 'two murderers' host
He was apparently referring to O.J. Simpson and Robert Blake (pictured)
Tom Hanks was skewering himself, as he was featured among the offensive 'ethnic stereotypes'
Rob Schneider made an appearance as a Mexican with a stereotypical mustache, sombrero and poncho as he spoke about NAFTA
Oscar nominee Adrien Brody's infamous Jamaican character, which he used to introduce Sean Paul, was also featured, and it was simply labeled, 'Whoa'
Among the sketches were several in which actors appeared in blackface or with darkened skin, though SNL opted to blur those faces
The show was also much more flippant about using racial slurs in the past, as illustrated by an infamous scene in which Chevy Chase and guest Richard Pryor traded off slurs
Some of the sketches were noted for being more recent than viewers might have thought, including an episode from 2000 in which guest host Lucy Liu joked that her mother had cooked a dog, referencing racist jokes about Asians
SNL also owned up to making light of child sexual abuse in several scenes, including one in which Mike Meyers appeared in a bathtub with a young Macaulay Culkin
The sketch pulled double duty as an example of sexual assault, as his character began to try to make out with the late Kirstie Alley.
Oscar nominee Adrien Brody's infamous Jamaican character, which he used to introduce Sean Paul, was also featured, and it was simply labeled, 'Whoa.'
Among the sketches were several in which actors appeared in blackface or with darkened skin, though SNL opted to blur those faces.
The show was also much more flippant about using racial slurs in the past, as illustrated by an infamous scene in which Chevy Chase and guest Richard Pryor traded off slurs.
After alternating, escalating curses, Pryor shouted 'honky,' leading the Vacation star to follow up with the N-word.
'Dead honky!' shot back the late comedian.
Some of the sketches were noted for being more recent than viewers might have thought, including an episode from 2000 in which guest host Lucy Liu joked that her mother had cooked a dog, referencing racist jokes about Asians.
SNL also owned up to possibly tasteless jokes referencing child sexual abuse in several scenes, including one in which Mike Meyers appeared in a bathtub with a young Macaulay Culkin.
The show also admitted to plenty of flagrantly sexist jokes, including a Weekend Update sketch in which the late Norm Macdonald said a poorly received joke was written by a woman, only to reverse it and joke that no women wrote for SNL
Ben Affleck illustrated the show's adoption of ableism in a sketch in which he lashed out at Fred Armisen, who was playing a developmentally delayed man who wasn't a fan of Chasing Amy
The show's history of sometimes using cringe-inducing gay characters was highlighted in multiple clips, including a short segment from the animated Ambiguously Gay Duo
But it was clear SNL wasn't suggesting that everything that made modern viewers uncomfortable was actually offensive
The show also admitted to plenty of flagrantly sexist jokes, including a Weekend Update sketch in which the late Norm Macdonald said a poorly received joke about women drivers was written by a woman, only to reverse it and joke that no women wrote for SNL.
Ben Affleck illustrated the show's adoption of ableism in a sketch in which he lashed out at Fred Armisen, who was playing a developmentally delayed man who wasn't a fan of Chasing Amy.
The show's history of sometimes using cringe-inducing gay characters was highlighted in multiple clips, including a short segment from the animated Ambiguously Gay Duo.
But it was clear SNL wasn't suggesting that everything that made modern viewers uncomfortable was actually offensive.
A scene of Will Ferrell insulting an adorable dog was included as an instance of 'animal cruelty,' but that only would have fit the bill if the dog understood fluent English.
