Movies Like Cum In My Hole Boss!

If you liked Cum In My Hole Boss! (2008), a movie directed by Dino Phillips, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
Weekend at Bernie's (1989)
★ 6.4/10
Two young insurance corporation employees try to pretend that their murdered employer is alive by puppeteering his dead body, leading a hitman to attempt to track him down to finish him off.
2
Secretary (2002)
★ 6.8/10
A young woman, recently released from a mental hospital, gets a job as a secretary to a demanding lawyer, where their employer-employee relationship turns into a sexual, sadomasochistic one.
3
Horrible Bosses (2011)
★ 6.6/10
For Nick, Kurt and Dale, the only thing that would make the daily grind more tolerable would be to grind their intolerable bosses into dust. Quitting is not an option, so, with the benefit of a few-too-many drinks and…
4
Disclosure (1994)
★ 6.2/10
A computer specialist is sued for sexual harassment by a former lover turned boss who initiated the act forcefully, which threatens both his career and his personal life.
5
Nine to Five (1980)
★ 7/10
Three female employees of a sexist, egotistical, lying, hypocritical bigot find a way to turn the tables on him.
6
Porno (2019)
★ 6/10
When a group of naive teens working at a movie theater in a small Christian town discover a mysterious film hidden in its basement, they unleash an alluring succubus who gives them a sex education…written in blood.
7
Office Space (1999)
★ 7.4/10
A depressed white-collar worker tries hypnotherapy, only to find himself in a perpetual state of devil-may-care bliss that prompts him to start living by his own rules, and hatch a hapless attempt to embezzle money…
8
Heatwave (2022)
★ 6.2/10
A woman's life takes an unexpected turn when she falls for her boss's wife. She must soon defend herself as she becomes entangled in a web of malice.
9
Mafia Mamma (2023)
★ 6/10
A suburban American woman inherits her grandfather’s Mafia empire and, guided by the Firm’s trusted consigliere, defies everyone’s expectations, including her own, as the new head of the family business.
10
The Only Living Boy in New York (2017)
★ 6.3/10
When a young man learns that his overbearing father is having an affair, he tries to stop it, only to be seduced by the older woman as well.
11
Set It Up (2018)
★ 6.9/10
Two overworked and underpaid assistants come up with a plan to get their bosses off their backs by setting them up with each other.
12
Swimming with Sharks (1994)
★ 6.6/10
Guy is a young film executive who's willing to do whatever it takes to make it in Hollywood. He begins working for famed producer Buddy Ackerman, a domineering, manipulative, coldhearted boss. When Guy also finds out…
13
Tomorrow, When the War Began (2010)
★ 6.1/10
Ellie Linton, a teen from an Australian coastal town, leads her friends on an excursion to a camp deep in the woods, dubbed "Hell." Upon their return, the youths find that their town has been overrun by an enemy army…
14
Innocent Blood (1992)
★ 6.2/10
Marie is a vampire with a thirst for bad guys. When she fails to properly dispose of one of her victims, a violent mob boss, she bites off more than she can chew and faces a new, immortal danger.
15
Focus (2015)
★ 6.9/10
Nicky, an accomplished con artist, gets romantically involved with his disciple Jess but later ends their relationship. Years later, she returns as a femme fatale to spoil his plans.
16
F.I.S.T. (1978)
★ 6.5/10
Johnny Kovak joins the Teamsters trade-union in a local chapter in the 1930s and works his way up in the organization. As he climbs higher and higher his methods become more ruthless and finally senator Madison starts…
17
Bombshell (2019)
★ 6.8/10
Bombshell is a revealing look inside the most powerful and controversial media empire of all time; and the explosive story of the women who brought down the infamous man who created it.
18
The Assistant (2020)
★ 6.3/10
A searing look at a day in the life of an assistant to a powerful executive. As Jane follows her daily routine, she grows increasingly aware of the insidious abuse that threatens every aspect of her position.
19
Citizen Toxie: The Toxic Avenger IV (2001)
★ 6/10
A horrific explosion creates a dimensional portal between Tromaville and its dimensional mirror image, Amortville. While the Toxie is trapped in the mirror dimension, Tromaville comes under the control of his evil…
20
Desperate Living (1977)
★ 6.3/10
After killing her husband, Peggy Gravel and her murderous maid Grizelda wind up in the crazy town of Mortville, where Queen Carlotta presides over a sleazy collection of misfits.