The glitz and glamour of Hollywood is a bright sheen over a city riddled with scandal and broken dreams. For every inspirational Tinseltown accomplishment achieved, there are millions of heartbreaking tales of failure. Something your favorite comedians are all-too-familiar with. 

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And so, here are some of the darkest jokes, sketches and scenes regarding the seediness of showbiz…

13 Dad’s Hollywood Secret

Key & Peele showcases just how unkind old Hollywood was to Black actors.

12 Black Acting School

Robert Townsend showcases just how unkind contemporary Hollywood is to Black actors. (Wait, are you getting a sense of deja vu?)

11 ‘Robot Chicken’ on Teen Actors

Robot Chicken looks at the problems teenage girls have when vying for a career in La-La Land.

10 Walt Disney’s “Casting Couch”

Family Guy brings attention to the sexually inappropriate and traumatizing experiences many actresses have gone through, but in animated mouse form.

9 ‘South Park’ on Hollywood Elites

In the town of South Park, a “tutoring company” teaches the kids the real dark history of Hollywood and how they maintain power.

8 Superstar

Mr. Show highlights the issues of children within show business and the poor parenting surrounding them.

7 ‘Good Will Hunting 2: Hunting Season’

Jay and Silent Bob Strike Back pokes fun at the malaise of creating a sequel — a violent, bloody sequel.

6 Patty Cake

Who Framed Roger Rabbit can take something as serious and dark as a conspiratorial affair in Hollywood and make it wacky as hell.

5 Norm Macdonald on Bill Cosby

“My buddy said the worst thing about Cosby was he was a hypocrite. I said, ‘I don’t think that was the worst part.’ To me, the worst part was the raping. Way up high. And then the second would be the drugging. Then, the third would be the scheming. But anyways, hypocrisy would be way down the fucking line, like on the fourth page. I’m no expert, but I think most rapists are hypocrites.”

4 ‘Family Guy’ on Harvey Weinstein… and Minions

3 ‘Key & Peele’ on Steve Urkel

Key & Peele go dark over the changes in the 1990s sitcom Family Matters.

2 Switcheroo

Saturday Night Live gets into the problems with reboots, but not the ones you’re thinking of.

1 Dave Chappelle on Harvey Weinstein

“Harvey Weinstein is probably the first person I’ve ever looked at a photograph of and was like, ‘Yeah, he rapes.’”

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