10 Most Disturbing SNL Cameos Because of What We Know Now
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VOICE OVER: Kirsten Ria Squibb
WRITTEN BY: Nick Spake
Some celebrity appearances haven't aged well... Join us as we examine Saturday Night Live cameos that feel uncomfortable in hindsight due to scandals, controversies, and revelations that emerged later. From legal troubles to personal struggles, these once-innocent appearances now carry a darker subtext that viewers couldn't have anticipated at the time. Our countdown includes O.J. Simpson's appearance during the 15th anniversary special, Jared Fogle endorsing diets, R. Kelly performing with Lady Gaga, James Franco joking about Instagram controversies, and Lindsay Lohan's eerily prophetic "Weekend Update" segment. Which SNL cameo do you find most disturbing in retrospect? Let us know in the comments!
Top 10 Disturbing SNL Cameos Because of What We Know Now
Welcome to WatchMojo, and today we’re looking at surprise appearances on “SNL” that play differently in retrospect.
After hosting for this time in May 2004, Lindsay Lohan dropped by the “Weekend Update” desk later that December. Tina Fey and Amy Poehler are concerned about their young mentee, fearing she isn’t eating enough. Lohan argues that Fey and Poehler aren’t the best mentors, claiming one sleeps around and the other is drunk. Before parting, Lohan says that she’s headed to a club. At the time, Lohan’s career was virtually scandal-free. Within the following years, though, she’d dominate the headlines with reports of substance use and excessive partying while also struggling with bulimia. Lohan has since made a comeback, even collaborating with Fey again, but this cameo now feels like an omen for one of the darkest chapters in her life.
“Freaks and Geeks” only lasted a season, but the series paved the way for future collaborations between James Franco and Seth Rogen. When Rogen hosted “SNL” for the third time in 2014, a few familiar faces dropped by, including his buddy Franco. Rogen claimed he pranked Franco by pretending to be a young woman on Instagram. This referenced real-life allegations that Franco had been inappropriate with an underage girl. His “SNL” cameo made light of the incident, which the public seemingly forgot about until 2018 when more accusations arose with lawsuits following. Rogen, who some felt enabled Franco’s alleged behavior, was doubtful he’d ever work with him again. Discussing Rogen in 2014, Franco said, “We had 20 great years together, but I guess it’s over.”
During her second hosting stint in February 2002, Britney Spears welcomed then-boyfriend Justin Timberlake on stage. The pop world’s defining power couple ended things the following month. The public later learned of the relationship’s dark side, which included an abortion that Spears had reservations about. Spears also made an “SNL” cameo in 2003, appearing alongside Will Ferrell on “Weekend Update.” The singer mentioned being hounded by the paparazzi, who don’t always get their facts straight. This was soon taken into overdrive as Spears became the media’s prime target. By the time more people seriously considered the negative impact the tabloids had on Spears’ mental health, the damage was done. Spears tried playing along at first, but after a while, forcing a smile was too painful.
Matt Damon is always a welcome presence. His cold open cameo in September 2018 was no exception. Damon appeared as Brett Kavanaugh, who President Trump nominated to serve on the Supreme Court. His nomination was called into question when multiple women accused the circuit judge of sexual misconduct. Kavanaugh maintained his innocence before the Senate Judiciary Committee, although his disgruntled behavior didn’t help. Damon’s hilariously spot-on impression emphasized why some found it ridiculous that Kavanaugh was even being considered for the job. That said, the decision ultimately fell to the Senate, who confirmed Kavanaugh 50–48. While Kavanaugh was never formally charged, he remains a controversial figure. This “SNL” sketch is now a reminder that Kavanaugh is on the nation’s highest court for the foreseeable future.
Speaking of Ben Affleck’s greatest loves, we go from Matt Damon to Jennifer Garner. During his Oscar acceptance speech a few months earlier, Affleck described his marriage to Garner as “work.” With some questioning Affleck’s word choice, Garner joined him on “SNL” to set the record straight. Although Garner wasn’t thrilled with his word choice either, Affleck concluded the monologue with a heartfelt declaration to his wife. Granted, he read this from a cue card, but it gave us the impression these two could work through anything. Two years later, the couple announced they were separating with their divorce finalized in 2018. Affleck rekindled his romance with Jennifer Lopez, but with that marriage ending, some have speculated if there’s still hope for the other Bennifer.
In 2013, Lady Gaga and R. Kelly collaborated on the song “Do What U Want.” Some found the pairing insensitive given Kelly’s history of sexual misconduct accusations. Gaga also later revealed she was a survivor of sexual assault. Since Kelly was acquitted of those past charges, most people didn’t bat an eye when he made a surprise appearance on “SNL,” performing the song with host Gaga. Kelly resurfaced at the end of the show alongside Gaga, who thanked him. Fast-forward several years, Kelly found himself at the center of more accusations, a documentary, an arrest, and a combined 31-year sentence. Amid Kelly’s downfall, Gaga pushed to remove “Do What U Want” from circulation. She’d probably like to forget his “SNL” cameo too.
When Robert De Niro hosted in 2010, P. Diddy was announced as a musical guest. While the audience expected Diddy to sing, they were surprised to see the rapper pop up in a sketch as well. Playing himself, Diddy introduces Blizzard Man, played by Andy Samberg. Although the others in the room are skeptical of Blizzard Man, Diddy compares him to the likes of R. Kelly. In reality, Diddy is the one who has drawn more parallels to Kelly as of late. Seeing Diddy get close to a twerking De Niro in drag only makes the sketch more uncomfortable looking back. Diddy proclaims that Blizzard Man is taking him to the top, but sometimes, the higher one climbs, the further they fall.
One of the original “SNL” cast members, John Belushi officially left the show in 1979. Although he never hosted, Belushi returned for a couple of cameos, including one on Halloween 1981. Owing the punk rock band Fear a favor, Belushi booked them as the musical guest. There was some disagreement about the performance, which involved slamdancers. Since Belushi agreed to make a silent cameo during the cold open, though, the band played and partied on. Fear’s rowdy performance made this one of the most notorious episodes ever. Adding to the infamy, Belushi died from an overdose less than a year later. Nobody knew it then, but as Belushi emerged from a bathroom stall and looked in the mirror, it’d be his farewell to Saturday Night.
The 2000s were a simpler time when we could watch a Jared from Subway commercial without cringing. Before he was a convicted predator and registered sex offender, Fogle was everywhere during the early 21st century - even “TV Funhouse.” What’s the only thing more unsettling than hearing Fogel voice an animated version of himself? Seeing the former Subway spokesman in the flesh! On the heels of winning multiple gold medals at the 2008 Summer Olympics, Michael Phelps hosted the “SNL” season premiere. Phelps portrays himself in a sketch, promoting a diet that allows people to eat whatever they want. While several individuals endorse the Michael Phelps Diet, Fogel isn’t one of them. Let’s just say we never want to hear Jared mention a footlong again.
Between his NFL career and the murder trial that would define the rest of his life, O. J. Simpson entered the acting world. “SNL” provided a platform for Simpson to test his comedic chops when he hosted in 1978. Leaving an impression, Simpson returned for a brief appearance during the show’s fifteenth anniversary special. Simpson presented an “SNL Moment” when he shared an intimate exchange with Bill Murray and Garrett Morris. Of course, he claims this was actually fellow Hall of Famer Walter Payton, who broke Simpson’s rushing record. Watching this now, all we can think about is Norm Macdonald sitting behind the “Weekend Update” desk a few years later, relentlessly making fun of Simpson’s legal troubles and enraging the higher-ups at NBC.
Which “SNL” cameo do you find the most disturbing? Let us know in the comments.
Welcome to WatchMojo, and today we’re looking at surprise appearances on “SNL” that play differently in retrospect.
#10: Lindsay Lohan
After hosting for this time in May 2004, Lindsay Lohan dropped by the “Weekend Update” desk later that December. Tina Fey and Amy Poehler are concerned about their young mentee, fearing she isn’t eating enough. Lohan argues that Fey and Poehler aren’t the best mentors, claiming one sleeps around and the other is drunk. Before parting, Lohan says that she’s headed to a club. At the time, Lohan’s career was virtually scandal-free. Within the following years, though, she’d dominate the headlines with reports of substance use and excessive partying while also struggling with bulimia. Lohan has since made a comeback, even collaborating with Fey again, but this cameo now feels like an omen for one of the darkest chapters in her life.
#9: James Franco
“Freaks and Geeks” only lasted a season, but the series paved the way for future collaborations between James Franco and Seth Rogen. When Rogen hosted “SNL” for the third time in 2014, a few familiar faces dropped by, including his buddy Franco. Rogen claimed he pranked Franco by pretending to be a young woman on Instagram. This referenced real-life allegations that Franco had been inappropriate with an underage girl. His “SNL” cameo made light of the incident, which the public seemingly forgot about until 2018 when more accusations arose with lawsuits following. Rogen, who some felt enabled Franco’s alleged behavior, was doubtful he’d ever work with him again. Discussing Rogen in 2014, Franco said, “We had 20 great years together, but I guess it’s over.”
#8: Britney Spears
During her second hosting stint in February 2002, Britney Spears welcomed then-boyfriend Justin Timberlake on stage. The pop world’s defining power couple ended things the following month. The public later learned of the relationship’s dark side, which included an abortion that Spears had reservations about. Spears also made an “SNL” cameo in 2003, appearing alongside Will Ferrell on “Weekend Update.” The singer mentioned being hounded by the paparazzi, who don’t always get their facts straight. This was soon taken into overdrive as Spears became the media’s prime target. By the time more people seriously considered the negative impact the tabloids had on Spears’ mental health, the damage was done. Spears tried playing along at first, but after a while, forcing a smile was too painful.
#7: Matt Damon
Matt Damon is always a welcome presence. His cold open cameo in September 2018 was no exception. Damon appeared as Brett Kavanaugh, who President Trump nominated to serve on the Supreme Court. His nomination was called into question when multiple women accused the circuit judge of sexual misconduct. Kavanaugh maintained his innocence before the Senate Judiciary Committee, although his disgruntled behavior didn’t help. Damon’s hilariously spot-on impression emphasized why some found it ridiculous that Kavanaugh was even being considered for the job. That said, the decision ultimately fell to the Senate, who confirmed Kavanaugh 50–48. While Kavanaugh was never formally charged, he remains a controversial figure. This “SNL” sketch is now a reminder that Kavanaugh is on the nation’s highest court for the foreseeable future.
#6: Jennifer Garner
Speaking of Ben Affleck’s greatest loves, we go from Matt Damon to Jennifer Garner. During his Oscar acceptance speech a few months earlier, Affleck described his marriage to Garner as “work.” With some questioning Affleck’s word choice, Garner joined him on “SNL” to set the record straight. Although Garner wasn’t thrilled with his word choice either, Affleck concluded the monologue with a heartfelt declaration to his wife. Granted, he read this from a cue card, but it gave us the impression these two could work through anything. Two years later, the couple announced they were separating with their divorce finalized in 2018. Affleck rekindled his romance with Jennifer Lopez, but with that marriage ending, some have speculated if there’s still hope for the other Bennifer.
#5: R. Kelly
In 2013, Lady Gaga and R. Kelly collaborated on the song “Do What U Want.” Some found the pairing insensitive given Kelly’s history of sexual misconduct accusations. Gaga also later revealed she was a survivor of sexual assault. Since Kelly was acquitted of those past charges, most people didn’t bat an eye when he made a surprise appearance on “SNL,” performing the song with host Gaga. Kelly resurfaced at the end of the show alongside Gaga, who thanked him. Fast-forward several years, Kelly found himself at the center of more accusations, a documentary, an arrest, and a combined 31-year sentence. Amid Kelly’s downfall, Gaga pushed to remove “Do What U Want” from circulation. She’d probably like to forget his “SNL” cameo too.
#4: P. Diddy
When Robert De Niro hosted in 2010, P. Diddy was announced as a musical guest. While the audience expected Diddy to sing, they were surprised to see the rapper pop up in a sketch as well. Playing himself, Diddy introduces Blizzard Man, played by Andy Samberg. Although the others in the room are skeptical of Blizzard Man, Diddy compares him to the likes of R. Kelly. In reality, Diddy is the one who has drawn more parallels to Kelly as of late. Seeing Diddy get close to a twerking De Niro in drag only makes the sketch more uncomfortable looking back. Diddy proclaims that Blizzard Man is taking him to the top, but sometimes, the higher one climbs, the further they fall.
#3: John Belushi
One of the original “SNL” cast members, John Belushi officially left the show in 1979. Although he never hosted, Belushi returned for a couple of cameos, including one on Halloween 1981. Owing the punk rock band Fear a favor, Belushi booked them as the musical guest. There was some disagreement about the performance, which involved slamdancers. Since Belushi agreed to make a silent cameo during the cold open, though, the band played and partied on. Fear’s rowdy performance made this one of the most notorious episodes ever. Adding to the infamy, Belushi died from an overdose less than a year later. Nobody knew it then, but as Belushi emerged from a bathroom stall and looked in the mirror, it’d be his farewell to Saturday Night.
#2: Jared Fogle
The 2000s were a simpler time when we could watch a Jared from Subway commercial without cringing. Before he was a convicted predator and registered sex offender, Fogle was everywhere during the early 21st century - even “TV Funhouse.” What’s the only thing more unsettling than hearing Fogel voice an animated version of himself? Seeing the former Subway spokesman in the flesh! On the heels of winning multiple gold medals at the 2008 Summer Olympics, Michael Phelps hosted the “SNL” season premiere. Phelps portrays himself in a sketch, promoting a diet that allows people to eat whatever they want. While several individuals endorse the Michael Phelps Diet, Fogel isn’t one of them. Let’s just say we never want to hear Jared mention a footlong again.
#1: O. J. Simpson
Between his NFL career and the murder trial that would define the rest of his life, O. J. Simpson entered the acting world. “SNL” provided a platform for Simpson to test his comedic chops when he hosted in 1978. Leaving an impression, Simpson returned for a brief appearance during the show’s fifteenth anniversary special. Simpson presented an “SNL Moment” when he shared an intimate exchange with Bill Murray and Garrett Morris. Of course, he claims this was actually fellow Hall of Famer Walter Payton, who broke Simpson’s rushing record. Watching this now, all we can think about is Norm Macdonald sitting behind the “Weekend Update” desk a few years later, relentlessly making fun of Simpson’s legal troubles and enraging the higher-ups at NBC.
Which “SNL” cameo do you find the most disturbing? Let us know in the comments.
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