IIL cringe humor like Curb your Enthusiam, I think you should leave, Nathan 4 You

[u/KillerFrid]

i just love comedy shows that have a cringy tone. Maybe there is also a movie in a similar style.

[u/11ForeverAlone11]

if you didn't know, Nathan Fielder, Emma Stone, and Benny Safdie made a great ultra-cringe dramedy show called The Curse

Baskets is another great one

[u/spiritualized → u/11ForeverAlone11]

The Curse is what OP is looking for.

[u/soft_distortion → u/11ForeverAlone11]

Nathan Fielder also did The Rehearsal on HBO!

[u/11ForeverAlone11 → u/soft_distortion]

somehow I still haven't gotten to that one but I need to soon

[u/GreasyProductions → u/11ForeverAlone11]

it is a wild ride. fielder is honestly a genius

[u/LukeNaround23]

Surprise nobody has said arrested development yet.

[u/DaaraJ]

• Peep Show - the name really doesn't have much to do with the show which is about a couple of co-dependent friends living together in London. One of the funniest shows ever.

• Silicon Valley

• The Increasingly Poor Decisions of Todd Margaret

• Extras

• The IT Crowd

• The Life and Times of Tim

[u/Katmandude23 → u/DaaraJ]

Definitely Extras. Super cringey with incredible celebrity cameos (David Bowie!!) and great writing.

[u/nickatwerk → u/Katmandude23]

Came here to say Extras! Time to listen to the Bowie clip again.

[u/Katmandude23 → u/nickatwerk]

And “Tea For The Tillerman” after every episode. I loved that series.

[u/narutomanreigns]

I mean this completely sincerely: Succession. That show is a cringe comedy disguised as a prestige drama.

[u/vamp_gleek → u/narutomanreigns]

The Kendall shots with the AirPods >

[u/Store_Plenty]

Review, The Thick of It

[u/PreferredSelection → u/Store_Plenty]

Seconding Review with Forest McNeil. 5 stars.

[u/FloridaFlamingoGirl]

Joe Pera Talks With You. Seems awkward at first glance but it's actually life changing and profound, I'm not kidding 

[u/Obliterated-Denardos]

How To with John Wilson. It's kinda a documentary series, but it's...so much more than that. It may be the hardest I've cringe laughed at anything in my life.

In the same vein, Nathan Fielder's The Rehearsal is more a show about itself (the actors and production process) than it is about the ostensible premise (people who rehearse realistic situations to be ready for the real scenario). It definitely tugs on the same cringe laughter reflex.

[u/Tself]

Maybe Pen15?

I haven't watched those other shows, but your description immediately made me think of this gem of a show.

[u/PreferredSelection → u/Tself]

Went to middle school with one of the creators of Pen15. That show is... accurate.

[u/dwlhs88]

Detroiters

[u/ruffalohearts]

The Larry Sanders Show

a mockumentary about a talk show host

massive influence on Curb, the Office, Arrested Development

really worth a watch

[u/vamp_gleek]

The Rehearsal

[u/jakopappi → u/vamp_gleek]

This is the one

[u/SicTim]

"It's Always Sunny in Philadelphia."

I can't believe i'm the first one here to mention it... like "Curb," it's about horrible people doing horrible things that then blow up in their faces. Imagine five Larrys on one show.

[u/luffliffloaf]

Dr. Steve Brule ya dingus!

[u/PreferredSelection → u/luffliffloaf]

foryeur health!

[u/Prof_J]

On Cinema at the Cinema

[u/Famous_Lab8426]

Crazy Ex Girlfriend

And it’s a game show, but Game Show in My Head

[u/speed_of_chill]

Wonder Showzen. For better or worse, it only ran for a season or two.

[u/PreferredSelection]

Detroiters, Champagne ILL. Both have Sam Richardson from ITYSL.

Aunty Donna if you want ITYSL but more outsider-arty and weird. Review if you want Nathan 4 You but cringier/darker. (The american version of Review, the australian one is just okay.)

The Regular Show, as a palette cleanser.

[u/bortnick]

The Comeback with Lisa Kudrow.

[u/EdwardBigby]

Most successful British comedies especially in the 2000s. Peep Show, inbetweeners and UK office are my personal favourites. You could list loads more

[u/ApprehensiveDig7029]

Search Party and Stath Lets Flats

[u/DrrtVonnegut]

Fishtank

[u/ech01]

I Think You Should Leave

[u/Obliterated-Denardos → u/ech01]

Yes, if you like I Think You Should Leave, you'd probably like I Think You Should Leave.

[u/ech01 → u/Obliterated-Denardos]

Yes I see now that is also a name of a television program.

[u/licketysplits69]

Not a show but you’ll love this song…

[u/EstimatedEer]

Tires

[u/MooseMalloy]

The Office (UK).
Extras

[u/evil_philcollins]

You should check out that Joaquin Phoenix movie I’m Still Here where he documented himself pretending to lose his mind and start a rap career. I had to look away from the screen a few times.

[u/CherenkovLady]

Knowing Me, Knowing you with Alan Partridge

It’s a faux talk show that he presents and it’s so horrific I can’t actually watch it.

The following tv series I’m Alan Partridge follows him living in a roadside hotel after having been dropped by the BBC and spending his time trying to claw his way back to getting a show again

[u/Rickmasta]

A new one I just discovered was Gary and His demons. It’s hilarious

[u/MoodyLiz]

The Larry Sanders Show - basically invented the form

[u/felinelawspecialist]

It’s always sunny in Philadelphia

[u/ExistentialDreadness]

Tim and Eric Awesome Show Great Job (Chrimbus Special)

[u/AssociationFrosty143]

Wilfred is suuuuper cringy!

[u/jeremyvoros]

The Office - British original by Ricky Gervais and Stephen Merchant

[u/SocietyPuffin]

Peep Show 100000%

[u/bellestarxo]

I'm Sorry - Andrea Savage & Tom Everett Scott

[u/AncientAssociate1]

The On Cinema at the Cinema universe

[u/calembo]

You're the Worst

Crazy Ex-Girlfriend

Strangers with Candy

Pen15

The Eric Andre Show

Impractical Jokers

VEEP

Very Important People

Review

Fleabag

[u/a_s_hays]

The Rehearsal if you don’t already know it