Horrible Bosses & 9 Other Hilarious Colin Farrell Roles, Ranked

Irish actor Colin Farrell has been in numerous movies and TV shows, many of which are quite good. He burst into major films with Phone Booth, and hasn’t stopped since. Although they tend to be more serious and frequently action-packed movies, there have been a few that add a heavy element of comedy to the mix.

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Even for those in the comedy genre, they still lean heavily towards crime and action- it seems like if he isn’t a criminal himself, he strongly tends to portray people who get mixed up in the rougher side of things. As you might expect in movies like those, the comedy leans to the darker side of things, but isn’t any less funny.

10 Fright Night (2011) – 6.3

A remake of an earlier 1985 horror movie of the same name, Farrell plays the new neighbor to the main character- who another teenager is convinced is a vampire. When it turns out he actually is, unsurprisingly, a vampire, he turns the teenager who suspected him.

Charley, the main character, finds a group of people willing to help him fight the undead threat and goes to war. An added bonus is David Tennant as a stage magician and supposed vampire expert, one of those slightly off-beat roles that Tennant excels at.

9 Intermission (2003) – 6.8

Farrell plays an Irish petty criminal who is constantly in some sort of trouble. Being both a crime film and Irish, it’s unsurprisingly a sometimes pretty dark black comedy. It revolves largely around the  consequences of a recent breakup between two of the other main characters, and the cascading events that are set in motion afterwards.

When the man decides to win his ex back he enlists the help of Farrell’s character, and things keep piling on top of one another as things go wrong one by one.

8 The Imaginarium of Doctor Parnassus (2009) – 6.8

This typically odd Terry Gilliam comedic fantasy wasn’t supposed to feature Farrell at all. The late Heath Ledger was part of the way through filming when he passed, and eventually Farrell, along with Johnny Depp and Jude Law, was brought in to play various versions of the main character as he travelled through a dream world.

The whole thing is offbeat in a way audiences have come to expect from Gilliam, and the sense of strangeness adds quite a bit to its comedic slant.

7 Horrible Bosses (2011) – 6.9

Farrell plays one of the three titular bosses. After the owner of the company Kurt (Jason Sudeikis) works for suddenly dies, his son Bobby (Farrell) takes over. Bobby has no idea what he’s doing, and causes Kurt to both begin to hate his job and worry that the whole company is going under.

It doesn’t help that Bobby is jealous of the closeness Kurt and his father shared, and makes his life miserable. Soon enough, Kurt joins two of his friends in a plot to rid themselves of their bosses once and for all.

6 Seven Psychopaths (2012) – 7.2

A writer who is working on his screenplay, also named Seven Psychopaths, Marty (Farrell) struggles with coming up with ideas for each of the seven characters. He’s helped with some ideas by his best friend Billy (Sam Rockwell), a petty criminal who kidnaps dogs and hides them until a reward is offered.

When a dognapping goes wrong, things start to cascade into a ludicrous situation, and they end up on the run from an angry mob boss who wants his dog back.

5 The Lobster (2015) – 7.2

Even for a movie described as an absurdist black comedy, The Lobster is both extra absurd and extra dark. After David’s (Ferrell) wife leaves him, he finds himself in a hotel. After he’s told he has 45 days to find a partner or be turned into an animal, David decides he’ll become a lobster.

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Residents of the hotel can hunt and tranquilize single people who live in the woods to give themselves more time, and things just get more and more absurd from there (even though it does end up being at least somewhat romantic).

4 The Gentlemen (2019) – 7.8

Colin Farrell and Charlie Hunnam in The Gentlemen

Yet another crime comedy, Farrell plays the coach of a group of young MMA fighters and aspiring YouTube stars. After they steal the marijuana from the lab of a big-time drug lord (and the main character, played by Matthew McConaughey) they upload a video of the heist to the internet, which for some reason is also a rap.

Coach goes to the lieutenant of the drug group to apologize for their raid and offer his services, and things start to snowball from there until multiple gangs are involved and events are starting to get out of hand.

3 In Bruges (2008) – 7.9

Ray in In Bruges

If you didn’t know, In Bruges focuses on, unsurprisingly, black comedy and crime. Farrell plays Ray, a young hitman who accidentally kills a kid in church while carrying out a hit on a priest. He, along with his mentor Ken (Brendan Gleeson, in one of his best roles), is sent to Belgium to wait until they’re called for after the uproar they’ve caused.

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Things start to get crazy even before Ken is ordered to kill Ray, and after Ken sends him away instead, the previous events come back to interfere with everything all over again. From then until the end of the film things just keep getting more and more ridiculous as the action builds.

2 Scrubs: My Lucky Charm – (2005) – 8.3

Colin Farrell scrubs

In this episode of the ever-popular sitcom, Farrell plays Billy Callahan, a charming Irishman who comes to visit his brother and woos practically everyone on staff. After it turns out he’s not so much the guy’s brother as he is the guy who punched him in a bar fight and sent him to the hospital in the first place, JD calls the cops and he’s arrested.

After everyone spends a while being angry at JD and Turk for being narcs, Billy returns to the hospital and everyone apologizes to everyone else. Billy’s brief time with them inspires JD and Turk to make their lives more exciting.

1 Sesame Street: The Whoosh and Vanish Mystery (2010) – 8.8

Colin Farrell Sesame Street

Sure, it’s an episode of Sesame Street, but it still manages to be as much of a crime comedy as an episode of a children’s show with Muppets can be, presumably because of Farrell’s presence (he joins a long list of celebrity guest stars on the show).

Farrell – as himself – and Elmo meet up, where they realized that neither of them know the word of the day. They set off to find it, and interview the characters they meet who give them clues about who knows it. Spoiler: the word is investigate.

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Updated: November 17, 2020 — 9:30 pm

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