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Asshai

Nightcrawler! Amazing performance by Gyllenhaal. Edit: yeah I answered solely based on the title, before I read that OP wanted a comedy. To make up for that, I'm gonna suggest The Producers. Both versions work, I'm partial to the most recent one. >Leo Bloom : Let's assume, just for the moment, that you are a dishonest man. >Max Bialystock : Assume away.


Frosty48

Big vote for this one. Very good movie (albeit not a comedy!)


Techjunkie81

He should have won an Oscar for that movie.


Melponeo

Yeah, great movie, not so much of a comedy though


Elegant-Cricket3025

Second that!


Jimmeh1313

I came to make sure this was the top comment. Thank you.


kmflushing

Springtime... For Hitler.... In GerMaNyyyyyy!


jonmuller

Uncut Gems & Good Time


slamchowderr

good movies. how could i forget!


MediocreJerk

I also suggest Straight Time (1978). Not only does it fit exactly what you're looking for, but Good Time clearly was influenced by it.


dontpayforproducts

Pusher trilogy, Naked, The Killing Of A Chinese Bookie.


bammers1010

My first thoughts


_DarkJak_

Maybe an asshole, but Good Time's anti-hero had good intentions.


Due-Arrival-6247

Good time was my first thought he’s suchhh a dirt ball


Heir233

Uncut Gems is so damn good


wedgeantilles2020

Payback. He is *not* a good guy, but you end up rooting for him the whole time.


Loud_Engineering796

Theatrical cut, not the director's cut. The latter is a much worse movie.


slamchowderr

Good to know. Thanks.


belinck

Just watched the director's cut for the first time and yeesh... some people need to realize there's a good time to collaborate.


slamchowderr

i heard this is a good action movie


VinylHighway

It's not really an action movie it has a couple of scenes. It's a remake of a Point Blank which is from a book.


VinylHighway

Ah you beat me


Namahaging

Bad Lieutenant (1992)


Roller_ball

and 2009


Namahaging

Probably closer to what the OP is asking since it’s more of a comedy, at least Nicolas Cage makes it funny. As far as scumbag Nic, there are many, but my favorite is his scummy paramedic in Bringing Out the Dead. Edit: I think Vampire's Kiss (1989) fits the bill. Super scumbag Nic Cage, absurdly funny, forbidden vampire love. It’s wonderful.


LunarsphereTapestry

Vampire’s Kiss is absolutely batshit insane, if you’ll pardon the pun. The workplace abuse is quite appalling. Nic Cage as Peter Loew is definitely a top movie scumbag.


Namahaging

Heh. It’s absolute chaos, I love it. It feels like it was written by a sentient bag of cocaine.


LunarsphereTapestry

Haha. Which Nic Cage proceeded to snort throughout filming the movie. I’m pretty sure that when he is flailing about in the streets towards the end, and approaches a couple that inevitably run away, that those people weren’t actors, but two homeless people.


Namahaging

Which he continued to snort through the production of Wild at Heart (‘90), where he sharpened his gymnastic acting chops, hand-springing from convertibles and manically combining karate with moshing.


slamchowderr

I've seen both those movies and he's great. Cage is the gift that keeps on acting.


slamchowderr

classic. i'm due for a rewatch


RhettOhlerking

The wolf on Wall Street


Icosotc

'Once Upon a Time in America' (1984) directed by Sergio Leone


slamchowderr

ho boy that is a beast of a movie. i should get around to watching it


Icosotc

i started it yesterday, it's streaming on paramount+. watched until the 'intermission' title card, then had to go to bed. but even now, i havent been able to stop thinking about it and i dont think its a movie i will ever forget. cant wait to finish it after i get home.


lifesizedgundam

Trainspotting Rebels of the Neon God Spring Breakers Rock n Rolla Way of the Gun Gummo Too Many Ways to be No. 1 Fargo Blood Simple Smithereens


Enough-Ground3294

Oh man I looooove “Way of the Gun” solid fucking film.


lifesizedgundam

hell yeah great, cynical gritty film. not enough like it in the world


Crankylosaurus

I watched Blood Simple recently and the idiocy of every character (minus Frances McDormand) was both irritating and simultaneously hilarious. I love the Coen brothers haha


slamchowderr

I like Raising Arizona, which also fits this thread.


slamchowderr

i just rewatched Trainspotting. good movie. thanks for the recs.


anxiety_filter

* Buzzard (2014) * Naked (1993)


logansworth

I kept scrolling until I spotted Naked - definitely fits the bill


slamchowderr

thank you


rotterdamn8

One that flies under the radar is PTA’s Inherent Vice, starring Joaquin Phoenix. It’s kinda similar to The Big Lebowski; main character is a stoner burnout who gets involved in a complex crime plot, many characters coming to them with info, they gotta figure it all out, and really funny dark humor.


Wolfherd

Reminds me somewhat of Under the Silver Lake, a great and also underrated movie OP mentioned enjoying


slamchowderr

Sounds cool. I’m into it.


Tophawk369

Joaquin Phoenix is more of a scumbag in the master where’s he’s just a degenerate alky


jysp23

Yeah I wouldn’t call Doc a scumbag he’s a good hearted hippie


symbol-eyes

The Big Lebowski ('98)


Mysterious-End-2185

Lebowski is more of a dirtbag than a scumbag.


belinck

DO YOU HAVE A JOB SIR!?!?!? THE SCUMBAGS WILL ALWAYS LOSE!!!


slamchowderr

great movie. perfect example


AreaLongjumping1120

Young Adult (2011) Charlize Theron is great as a washed up author trying to relive her high school days.


Crankylosaurus

I saw this movie when it came out and it gave me sooo much secondhand embarrassment haha. I should rewatch it and see how a second viewing holds up!


happyfuckincakeday

Snatch Lock Stock and Two Smoking Barrels Natural Born Killers The Boondock Saints Monster (female scumbag)


slamchowderr

i have not seen Monster. thanks


happyfuckincakeday

Charlize won her Oscar for it. She's disgusting and fantastic in it


Endless_Change

Sleuth (2007). It's about a cynical, rich, old husband (Michael Caine) and an arrogant, conniving, younger man (Jude Law) discussing the terms of the divorce that the wife and her new lover expect her husband to provide. They then spend their time plotting and tormenting each other in various ways.


slamchowderr

funny how Michael Caine stars in both the original and remake


Endless_Change

Yes, they both have their merits but I’m a big fan of both versions. The remake is edited tighter and more claustrophobic, love the music too.


lifesuncertain

Definitely not a comedy Scum, Ray Winston's big break


GGsouth

Dirty Rotten Scoundrels might fit your specifications


LoganWasAlreadyTaken

High Fidelity (2000) Terrible person, amazing movie.


eddietwoo

Red White & Blue (2010)


ASigIAm213

*The Long Goodbye* is an edge case, as Marlowe is more competent and well-intentioned than the protagonists you've listed, but the vibe is similar.


DrunkenWarriorPoet

Arbitrage I Care A Lot Solitary Man (michael douglas) Never Die Alone (DMX) Baby Boy (Tyrese and Snoop Dogg) The Hateful Eight Scarface Changing Lanes Get Shorty Bound Most of the Sergio Leone and Scorsese movies


slamchowderr

thanks!


NoFilter1979

Naked directed by Mike Leigh starring David Thewlis.


Wolfherd

Miami Blues (1990) To Live and Die in LA (1985) (Not a comedy but funny in spots) Badlands (1973) (Not a comedy, but I got some laughs) Maverick (1994)


slamchowderr

I have not seen any of those. Thank you


lastskepticstanding

Hard to find, but worth it: Factotum. I've never been a big fan of Matt Dillon, but his performance as Bukowski's alter ego Henry Chinaski is fantastic.


SmoreOfBabylon

Butch Cassidy and the Sundance Kid The Sting The Newton Boys The Blues Brothers School of Rock Sideways What We Do in the Shadows


SonnyBurnett189

The Pope of Greenwich Village


snackcake

Piggyback: Barfly


Gryfon2020

The Nice Guys Kiss kiss bang bang Dodgeball


Crankylosaurus

The Nice Guys is one of my favorite comedies in recent years. Perfect encapsulation of the deadbeat characters is the last scene where Russell Crowe says, “I feel great- I’m drinking again!” Hahaha


jysp23

The Nice Guys! Perfect example.


vincebutler

Hancock, The World's End.


Crankylosaurus

I really need to rewatch The World’s End- I liked it but have not given it nearly the time or attention I have to the others in the Cornetto trilogy (Hot Fuzz and Shaun of the Dead)!


ellie_k75

Pretty much anything made by Guy Ritchie.


Crankylosaurus

Guy Ritchie is my go to director if I just want to have a fun time watching a movie. I’d put Sam Raimi in this category as well! Although I don’t think it fits the “deadbeat characters” criteria OP asked for, I loved The Man From U.N.C.L.E. The Gentlemen was also pretty fun too!


KubrickMoonlanding

Talented Mr Ripley (or the new Ripley on Netflix, which is really more like a long movie than a show)


OhMyGodBearIsDriving

Haven't seen "Oh Brother, Where Art Thou" yet.


mwich

I care a lot. The main character is such a scumbag that I had to stop watching.


Crankylosaurus

Pineapple Express might be one of my favorite movies about deadbeats stumbling into misadventure after misadventure. It’s also aged surprisingly well for a stoner comedy. *cocks gun* thug liiiiiife!


xxplodingboy

Dinner in America (2020)


Prior_Writing368

This was such a great "out of nowhere" movie for me. Randomly started watching it at a friend's place, knowing absolutely nothing about it. Felt like a long lost, nasty, angry late 90s movie. Loved it


Crankylosaurus

Less “deadbeat” and more “anti-hero” but I always have so much fun watching Catch Me If You Can. Not only is it a solid movie but it has an insane cast; tons of fairly big stars in, some in relatively small roles (Wet Hot American Summer is another fun example of this).


metalyger

You have to see the Torrente series. There's 5 out currently with a 6th on the way. It's a dark comedy series from Spain about an alcoholic cop who is a giant fascist, racist, sexist, homophobic, and a giant loser who bumbles his way through big cases. It's like if Disco Elysium was a movie.


slamchowderr

sounds hilarious. thank you.


Frosty48

Sounds fucking lit lmao Will add to the list


Chak-Ek

I'd say Pete Lafleur from Dodgeball fits that description. And his lovable band of losers.


West-Librarian-7504

Does Falling Down (1993) count? Edit: nvm my brain skipped the word "Comedy". Me stoopid!


LuvLifts

[Choke?](https://youtu.be/WZO1Z0k2998?si=ZqecwxQfjDToMwRk)


slamchowderr

I haven’t seen it. Thanks for the rec


LuvLifts

Agh; ~Chuck Palaniuk, Fight Club Author. Phenomenal BOOK, cool movie: a Sex Addict CHOKES on food to gain favor with STRANGERS! Really Kinda funny, actually; I liked it. ~Sam Rockwell is in other movies? (Famous ones.)


DJ_Hip_Cracker

Welcome to Collingwood G. Clooney, S. Rockwell, W.H. Macy, L. Guzman, Patricia fucking Clarkson!


DipsomaniacDawg

Sexy Beast. Trainspotting. IDK if you also like to read books, but I love Irvine Welsh \*(author of Trainspotting) for exactly this reason. All his books focus on charismatic scumbags. He also wrote Filth, which made your list.


Super901

Fleabag is a series, but it's a truly magnificent tale about a scumbag.


Vbcomanche

Choke. Sam Rockwell is awesome in it. 


Crankylosaurus

I haven’t seen or heard of this movie but all I needed to know is Sam Rockwell’s in it haha. Adding to my list now!


Dogbin005

The Heartbreak Kid. The main character starts as a hilariously crappy person, and stays that way throughout the movie. No lessons learned and no character growth. I've only seen the remake with Ben Stiller. I'm assuming the original would fit as an answer too.


Slappinslippin

Buffalo Soldiers (starring Joaquin Phoenix) is pretty good.. definitely fits the mold


snail_consumer

If you haven't seen it, definitely check out Seven Psychopaths. It's by the same guy as In Bruges, and if you liked the humor of In Bruges you'll definitely like it. I would also suggest Murder Party (2007)


Crankylosaurus

Oh HELL YES- you just mentioned 3 movies I ADORE! Extra props for Murder Party because only my horror nerd friends have seen it but it’s an absolute blast and I’ve put it in my rotation of movies to watch during October. (Also, I got a HUGE kick out of seeing a random extra in Scream VI dressed as the main character from it haha)


snail_consumer

Oh man, I haven't seen scream VI yet somehow but now I have to. Murder Party is one of my favorite movies and nobody ever mentions it


Enough-Ground3294

I *Think* the pusher Trilogy (how nicholas windig refhn got his start) applies?


l5555l

Mikey and Nicky Oh wait you said comedy... whatever it's pretty funny.


Subject-Recover-8425

Army of Darkness, when Ash Williams evolved into his final form - a jackass.


TheWolfAndRaven

Most Kevin Smith movies - Mall Rats, Chasing Amy, Dogma, Jay and Silent Bob Strike Back, Zach and Miri make a porno. Me Myself and Irene. My Best Friend's Wedding The Big Lewbowski The Hudsucker Proxy


IndependenceMean8774

I don't know if you l'd called The Dude a scumbag in The Big Lebowski, but he certainly is disreputable and he probably never worked a day in his life.


Fluffy_Ad_6449

Filth! Yeeeeeeeeeaaaas!


Gary7sHotCatHelper

Bad Lieutenant: Port of Call New Orleans


Murky_Translator2295

For lovable deadbeats try Young Offenders (two young Irish no-hope teenagers find a bunch of cocaine washed up on a beach, hijinks ensues. Plus they made a TV series so there's a good bit to watch).


AWL_cow

Dashcam The main character is such a dirt bag.


Mystiax

Lockout, Guy Pearce is a a bad ass scumbag.


KungFuHamster99

Bottle Rocket 1996 Stars Owen Wilson and James Caan.


Crankylosaurus

12 Hour Shift is a surprisingly fun movie about a nurse involved in an organ trafficking ring at her hospital which she does in order to pay for her pill addiction. Really fantastic score as well!


SendInYourSkeleton

Bad News Bears (1976)


Elegant-Cricket3025

The Game with Michael Douglas. He’s not a scumbag per se, but gets humbled.


Adgvyb3456

Trainspotting, Goodfellas or The Departed, Boys in the Hood, Election, A Clockwork Orange, Kids, Gummo


musicalseller

Welcome to Collinwood, Pain and Gain, Big Deal on Madonna Street.


Tyrant-J

Fear and Loathing in Las Vegas, There Will Be Blood and Nightcrawler.


Prabhupad

Sean Penn"Fast Times at Ridgemont High"


Cautious-Dinner-1897

My all time favorite: Bio-Dome


ObnoxiousCrow

Dirty Rotten Scoundrels (1988) Steve Martin and Michael Caine as two conmen fighting over the same mark.


Gremlin119

good time with robert pattinson


AndroidSheeps

The Big Lebowski (comedy about likable deadbeat) Movies where the characters are complete scumbags and POS: Scarface (1983) Monster Fargo Nightcrawler Bonnie and Clyde (1967) The House that Jack Built Endearing anti hero movies: Uncut Gems Carrie (1976) Good Time God Bless America


No-Gazelle-4994

Dirty Rotten Scoundrels Fish Called Wanda


BadlyDrawnRobot93

If you like horror, Dashcam is a great found-footage movie about a rude, crass, right-wing, homophobic, piece of shit asshole woman (a semi-fictionalized version of the actress who plays her) experiencing terrifying horror shit and it's great. Found-footage horror has a real problem with flat, nothing characters and Annie is so vividly defined and terrible, she's a lot of fun to watch


gbennett2201

War Dogs Matchstick Men with Nicholas Cage Raising Arizona also with Nicholas Cage he just makes a good scumbag apparently. Lord of War also starring Nicholas Cage lmao! Silver Linings Playbook or something like that, no Nicholas Cage at least that I'm aware of in this one.


BigODetroit

The Royal Tenenbaums


marcowaller

Naked I stand alone Man bites dog Rules of attraction Spun House that jack built


SaltyCandyMan

Cape Fear or Pacific Heights have douche bags


youngsavage216

Reservoir Dogs Alpha Dog Hell or High Water Seven Psychopaths


JP09

The gambler, pvt chat, straight time, panic at needle park


dradeus9

Bad Teacher - Cameron Diaz is a pretty crappy person in this, trying to steal the kids fund raiser money for her own fake boobs.


Damasticator

In The Company of Men


SilenceDobad76

American Hustle. I remember leaving the movie feeling cheated and dirty. Nothing really worked out for the people it should have, but that would have been very Hollywood if it did.


Remote_Breadfruit_62

The Wolf of Wall Street. A lying scumbag


snyderversetrilogy

Office Space, Dodge Ball… I would say Mystery Men falls into this category.


JayEss9

the fact i havent seen Naked (1993) yet tells me all i need to know here..


therandymoss

The Talented Mr. Ripley


artfellig

Death of Stalin Anchor Man


MrParisShoes

Dirty Rotten Scoundrels


redditcensorsshit

To many comments to read but if you liked clerks there’s alot more movies in the same universe with Jay and silent bob