The WORST episodes of Dark Side of Comedy

Every episode of Dark Side of Comedy ever, ranked from worst to best by thousands of votes from fans of the show. The worst episodes of Dark Side of Comedy!

Explore the intensely personal journeys of the world’s most beloved comics, and the struggles that they encounter behind the mask, through first-person storytelling, incredible archival, and evocative recreations.

Last Updated: 5/11/2026Network: VICE TV (US)Status: Continuing

6.82

33 votes

#1 - Ellen DeGeneres

Season 2 - Episode 8 - Aired 12/5/2023

Ellen DeGeneres revolutionized TV with a unique brand of positive humor, but behind the scenes a massive controversy was brewing--one that would tarnish her image forever.

Watch Now:Amazon

7.00

36 votes

#2 - Carlos Mencia

Season 2 - Episode 4 - Aired 11/7/2023

Carlos Mencia was one of the biggest comics in America until accusations of joke theft led to one of the most dramatic downfalls in comedy history.

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7.11

65 votes

#3 - Andrew Dice Clay

Season 1 - Episode 2 - Aired 8/23/2022

Andrew Dice Clay's controversial brand of comedy found a huge base with white men in America.

Watch Now:Amazon

7.12

51 votes

#4 - Roseanne Barr

Season 1 - Episode 3 - Aired 8/30/2022

Roseanne Barr made a name speaking her mind but her impulse may have cost her her career.

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7.15

34 votes

#5 - Maria Bamford

Season 1 - Episode 10 - Aired 10/19/2022

How Maria Bamford channels her mental illness into comedy, and encourages others to do the same.

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7.16

38 votes

#6 - Family Matters

Season 2 - Episode 7 - Aired 11/28/2023

Family Matters was one of the most wholesome sitcoms of the 90s, but the success of the show led to issues for many cast members who are still dealing with trauma and addiction.

Watch Now:Amazon

7.18

33 votes

#7 - Tracy Morgan

Season 2 - Episode 6 - Aired 11/21/2023

Tracy Morgan survived drug-dealing, hyper-competitive SNL, and substance abuse. But a brutal car accident and two-week coma made him finally confront his childhood demons.

Watch Now:Amazon

7.21

38 votes

#8 - Sam Kinison

Season 2 - Episode 2 - Aired 10/24/2023

Sam Kinison revolutionized comedy with a vulgar, sexist act, but his appetite for cocaine and chaos would lead to a dramatic downfall at the height of his massive success.

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7.24

34 votes

#9 - Gilda Radner

Season 2 - Episode 10 - Aired 12/19/2023

Gilda Radner was SNL's first female star. But her pioneering success was plagued by trauma, eating disorders, heartbreak and cancer, all of which she turned into comedy material.

Watch Now:Amazon

7.25

36 votes

#10 - Brett Butler

Season 1 - Episode 8 - Aired 10/5/2022

Money. Success. Respect. Brett Butler had it all. Here's how the fiercely original stand-up and sitcom star gained everything... only to lose it all.

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7.28

36 votes

#11 - Freddie Prinze

Season 1 - Episode 9 - Aired 10/12/2022

A working class Peurto Rican kid, Freddie Prinze exploded onto the comedy scene but his overnight fame came to an abrupt end.

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7.41

37 votes

#12 - Joan Rivers

Season 2 - Episode 3 - Aired 10/31/2023

Joan Rivers' insults made her a comedy icon, but the pressures of a male-dominated industry led to eating disorders, self-loathing, and a deadly addiction to plastic surgery.

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7.41

46 votes

#13 - Dustin Diamond

Season 1 - Episode 6 - Aired 9/20/2022

Dustin Diamond found fame but when it ended, Dustin was lost, descending into one tragic chapter after another.

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7.45

38 votes

#14 - Norm MacDonald

Season 2 - Episode 9 - Aired 12/12/2023

On SNL and beyond, Norm MacDonald was legendary for his fearless comedy. But his controversial persona concealed a serious gambling problem and a secret that he took to his grave.

Watch Now:Amazon

7.52

33 votes

#15 - Phil Hartman

Season 2 - Episode 5 - Aired 11/14/2023

Phil Hartman was a beloved SNL and Simpsons cast member, but his squeaky clean image was at odds with a toxic marriage that descended into a tragic murder-suicide.

Watch Now:Amazon

7.53

51 votes

#16 - Artie Lange

Season 1 - Episode 4 - Aired 9/6/2022

Artie Lange enjoys mainstream success as a comedian, but his addiction to heroin, coupled with childhood traumas, threatens to thwart his ambition and life.

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7.58

65 votes

#17 - Chris Farley

Season 1 - Episode 1 - Aired 8/16/2022

Struggling with addiction and a low self-image, Chris Farley's friends at "Saturday Night Live" conspired to help save him.

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7.60

47 votes

#18 - Richard Pryor

Season 1 - Episode 5 - Aired 9/13/2022

Richard Pryor confronts America with brutal honesty, but while he fights for a voice on stage, he is losing his own battle to drugs and family trauma.

Watch Now:Amazon

7.62

47 votes

#19 - Greg Giraldo

Season 1 - Episode 7 - Aired 9/27/2022

Roastmaster. Road warrior. Addict. Dad. How beloved comedian Greg Giraldo's career - and life - was sabotaged by a toxic mix of addiction and self-loathing.

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7.85

40 votes

#20 - Robin Williams

Season 2 - Episode 1 - Aired 10/17/2023

Robin Williams’ suicide shocked the world. While he was one of the most successful comedians ever, he was struggling privately with crushing health and psychological issues.

Watch Now:Amazon