After steadily building a career in standup comedy, Wayans scored his first movie role in 1984, making a brief appearance in Beverly Hills Cop as a hotel employee selling bananas. The scene put him face-to-face with Eddie Murphy, the SNL star who was in the midst of a meteoric rise in Hollywood.
A year later, Wayans joined the Saturday Night Live cast for Season 11, the show’s first following Murphy’s departure. Though the two African American comedians had very different styles, the optics were hard to ignore: To most at home, Wayans was brought on as Murphy’s replacement.
Aware of how this looked, SNL producer Lorne Michaels (who himself had just come back to the show) was hesitant to give Wayans much screen time.
“Lorne Michaels was trying to — he thought — protect me from being compared to Eddie Murphy,” Wayans recalled in a 2015 interview with the Breakfast Club radio show. “And I’m like, ‘Look, you give me the ball or let me go. Fire me from the team.’”
According to David Peisner, author of Homey Don’t Play That: The Story of ‘In Living Color’ and the Black Comedy Revolution, Murphy had actually given Wayans the following advice prior to the latter’s SNL debut: “Don’t get integrated into the cast. If you want to stand out, write your own sketches. Even if you only do one sketch, make sure it’s centered around you. Otherwise, you get sucked in and become Garrett Morris.”
Morris was SNL’s first Black cast member, part of 1975’s original Not Ready For Prime-Time Players. The comedian often played smaller, background roles while breakout stars like John Belushi, Chevy Chase, Bill Murray and Dan Aykroyd enjoyed the spotlight. Wayans wanted to stand out, much like Murphy had before him. To that end, he pitched various sketch ideas on a weekly basis, only to have them rejected. Instead, Wayans was given smaller roles, sometimes with no lines at all.
“They had me in scenes where I would just hold a spear,” Wayans later recalled. “I’m like, ‘I’m not doing that. My mother’s going to watch this show.’ No lines! Just holding the spear in a thong. I’m like, ‘I can’t do this.’ I said, ‘Y’all need to hire an extra for this.’ And so they told me, ‘You’re not a team player.’ I said, ‘No, I’m just not a slave.’
Tension behind the scenes was building, compounded by the show’s low ratings. Many questioned whether the series would survive without a breakout star like Murphy. Wayans exacerbated things by wearing sunglasses in the show’s studios and proclaiming, “It’s too white in here. It hurts my eyes.”
“I created a tension in there,” the comedian admitted. “And it was only because they wouldn’t let me – you know, comedy is tension, but then you break the tension, that’s where the laugh comes. But they just wanted me to be too submissive, and I couldn’t.”
The final straw would snap on March 15, 1986. Wayans was set to play a police officer in a sketch titled “Mr. Monopoly,” which was structured to be a spoof of Miami Vice. In dress rehearsal, Wayans wore a suit, similar to what Crockett and Tubbs wore on the popular action show.
After running through the scene, Michaels approached Wayans. “You look like a pimp in that suit,” the SNL producer reportedly remarked. “I want you to change it to a cop’s uniform.” “I just snapped,” Wayans admitted, explaining that such micromanaging in a sketch that he already thought “wasn’t funny” added insult to injury. “So, I was just like, you know what, I’m done. And I just flipped characters.”
Watch the ‘Mr. Monopoly’ Sketch From ‘SNL’
When the “Monopoly Man” sketch went live, Wayans played his character as an over-the-top, effeminate homosexual stereotype. It wasn’t how the scene was written — and it wasn’t what any of the cast or crew expected either. An added layer of awkwardness was palpable during the sketch, which didn’t get many laughs. “I was angry. That’s the reason why it wasn’t funny,” Wayans admitted years later to The Weekender. “It was right after Eddie Murphy left the show and they weren’t letting me do things that he would do. So, I went against the script. That was my frustration.”
Michaels fired Wayans on the spot, ending his SNL tenure after only 12 episodes as a cast member. “He was right to fire me,” the comedian later admitted. “I wanted to get fired.”
Wayans’ star took off after his brief SNL career. Alongside his older brother Keenan, he starred the sketch comedy show In Living Color, which became a pop-culture phenomenon in the ‘90s. “All the stuff I was trying to do on Saturday Night Live was actually stuff I was able to do on In Living Color,” he later noted.
Still, there were no hard feelings between Wayans and Michaels. In fact, the comedian was invited back to host the show on April 8, 1995.
Watch Damon Wayans’ ‘Saturday Night Live’ monologue from 1995