Sean 'Diddy' Combs Movie & TV Show Cameos That Are Really Creepy In Hindsight

The following article contains mentions of sexual assault and child abuse. 

Sean "Diddy" Combs has gone from a popular artist, producer, and record company mogul to one of the most controversial figures in entertainment. He was arrested in September due to allegations of systematic and long-running sexual abuse and is facing lawsuits for sex trafficking, sexually assaulting minors, and other alleged crimes. 

Combs' lengthy entertainment career has made him a highly visible figure — not only in music but also in movies and on TV shows. Over the years, he has appeared in several productions, in roles that range from quick cameos to outright main characters. Due to the nature of the allegations against him, some of his parts have become extremely creepy in hindsight. Here's a look at the most uncomfortable ones. 

Comedy music group The Lonely Island's journey from Berkeley to internet stardom was built on "Saturday Night Live" digital shorts that often feature celebrities. In 2013, they released their third full-length album, "The Wack Album." Sean Combs appears in the music video for their song "Go Kindergarten," and with the benefit of hindsight, the end result is a solid contender for the "most uncomfortable three minutes ever filmed" award. 

The video begins when Combs enters a club with Paul Rudd and tells the actor to follow his lead. The two then move to the dance floor to watch The Lonely Island and Robyn perform the song, which instructs the partygoers to let their hair down with a series of increasingly outlandish actions. Unfortunately, said actions include Combs enthusiastically exposing himself, physically assaulting people, and performing all sorts of choreographed awfulness — up to and including cutting Rudd's middle finger off with garden shears. When a clearly frightened Rudd attempts to escape the club, a group of men in suits and sunglasses stop him from leaving, forcing him to stay at the party against his will.  

Technically speaking, Combs is just doing what the song's lyrics suggest. However, the whole video is coded to imply that he fully knows what's about to go down, and that he — unlike Rudd — retains control of the awful situation throughout. All in all, not a good look.

The 2010 comedy "Get Him to the Greek" is a key part of Jonah Hill's transformation from "The 40 Year-Old Virgin" to today, being the actor's first starring role after 2007's "Superbad." Hill plays lowly record company talent scout Aaron Green, who hatches a plan to resurrect the career of washed-out rocker Aldous Snow (Russell Brand) with a 10-year anniversary concert of his greatest performance at the Greek Theatre in Los Angeles. Shenanigans ensue. 

Sean Combs has a fairly large role in the movie as music mogul Sergio Roma, the head of Aaron's record company. Sergio is not only a bad boss, but a deeply violent and abusive man who brags about his wealth and shoots down everyone else, from his own assistants to Pharrell Williams. Watching Combs' character browbeat underlings into terrified submission and physically beat up people is deeply uncomfortable considering the real-life allegations against him. 

If Combs' presence wasn't enough to make "Get Him to the Greek" a tough watch, his co-star Brand is also facing serial rape allegations. Fans of Brand's bohemian character may also be less than thrilled to discover that the comedian has reinvented himself as a conspiracy theory-spewing right-wing darling in the wake of the COVID-19 pandemic. 

In 2015, Sean Combs guest-starred on the Season 1 finale of the ABC sitcom "Black-ish" as gangster Elroy Savoy. Much of the episode takes place in the past, as Pops (Laurence Fishburne) relays a story of his family members' adventures in the 1920s, where ice delivery man Drexler Johnson (Anthony Anderson) ends up on a collision course with Harlem club owner Savoy. 

Combs as an abrasive Jazz Age villain is precisely as creepy as you'd suspect. As soon as we see him, Combs' character demands "two girls and four bottles." He then proceeds to verbally assault workers multiple times, overshare personal information about his nether regions, and generally act like a spoiled but dangerous brat throughout his time on-screen. What's more, the show seems to actively blur the line between the performer and the character by peppering the episode with references to Combs' own music and his record company, Bad Boy Records. 

"It's Always Sunny in Philadelphia" Season 8, Episode 6 is titled "Charlie's Mom Has Cancer." The FX sitcom tackles this sensitive subject in its usual irreverent way, but the episode also has an unfortunate guest star in Sean Combs. Here, Combs plays someone who's a far cry from his usual well-dressed and powerful characters, but his Dr. Jinx still has elements that come across as creepy in hindsight. 

Jinx is a vaguely threatening, smooth-talking musician who resides in a storage unit. The gang pays him a visit under the assumption that he's a doctor. Jinx happily plays along, to the point that he gleefully misdiagnoses Mac's (Rob McElhenney) eczema and cons him into accepting a supposed homeopathic treatment. This later turns out to be a dangerous pesticide spray that dramatically worsens the condition. Jinx even throws in a Bill Cosby reference — which is saying something because the episode came out in 2012, at which point allegations of Cosby drugging and assaulting women had already been out for years.  

Sean Combs' annual VIP "White Parties" have played a significant part in his public image both before and after his downfall, and ongoing lawsuits are looking into the many alleged illegal things that went on during such parties. As such, it's easy to do a spit-take when you see his 2009 two-episode guest-star turn on "CSI: Miami." 

The "CSI: Miami" character everyone forgets Combs played is the Season 7 defense attorney Derek Powell, who initially opposes Horatio Caine's (David Caruso) team in an important case but ultimately provides them with critical information. This is a fairly cut and dry role ... that is, until Powell returns on the episode "Sink or Swim," which opens with the character hosting a yacht party where several people are wearing white. Though Powell isn't exactly an antagonist here, it doesn't really help the situation that a woman dies at the end of the scene. 

If you or anyone you know has been a victim of sexual assault or child abuse, please contact the following resources: 

- Visit the Rape, Abuse & Incest National Network website or contact RAINN's National Helpline at 1-800-656-HOPE (4673).

- Contact the Childhelp National Child Abuse Hotline at 1-800-4-A-Child (1-800-422-4453) or their live chat services.