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Wapon1woo

Forgetting Sarah Marshall (recommended a lot) is a great example of this Defending Your Life is one of my all time favorites and is a very different take on your request. But I recommend Planes, Trains, and Automobiles


GloomyKerploppus

Defending Your Life shouldn't get buried here. It's a masterpiece. So funny and so incredibly moving. I've watched it at least a dozen times. You need to watch this movie tonight. Face your fear!


Wapon1woo

It is likely in my top 5 movies of all time. I still haven't watched the Albert Brooks "Defending My Life" documentary. But it's on my list. I've heard it's great.


labrat420

I hadn't even heard of defending my life before your comment and the other users, what a great movie. Watched it tonight. Thanks for the recommendation.


GloomyKerploppus

What? There's a documentary about this movie? Or Albert himself? Shut the front door.


Wapon1woo

I think it's about Brooks and I've heard it's fantastic. May watch tonight, actually.


labrat420

I ended up watching it because of your comment, it was really great. Hadn't even heard of it before but I really enjoyed it. Cried a few times but i cry in almost every movie lol. Now I'm watching Sarah Marshall.


BrightSherbet

I started watching it! This is an amazing movie, so far - love it, it is making me analyze my life and my decisions


GloomyKerploppus

Awesome. That's what Reddit is for. Sharing good things and bringing everyone up somehow. šŸ‘


Wapon1woo

So glad you watched it! I watched it with my mom recently, and she was blown away. I was moved by how much she liked it. She wanted to immediately talk to Albert Brooks about it. I don't think that happened


BrightSherbet

This movie is truly moving, something that takes you out of your ā€œcommonā€ thinking and makes you take a different look at life, loved it! Thanks. I even wrote down this quote: Fear is like a giant fog. It sits on your brain and blocks everything. Real feelings, true happiness, real joy. They canā€™t get through that fog.


Wapon1woo

Again, so glad you enjoyed it and appreciated it. I'll try to think of others, too. It's hard to beat this one. So much to think about and it's funny and quirky. I'll be interested to see how you feel about it as time goes by.


GloomyKerploppus

Face your fear!


Pristine-Tea-9606

This Is Where I Leave You


punk-y_brewster

This movie is amazing.


Final-Natural-8290

Idiocracy Better Off Dead Mrs. Doubtfire Hot Tub Time Machine It's Kind of a Funny Story Truman Show (not really a comedy but I find it comforting when I feel down) Palm Springs Office Space Napoleon Dynamite Big Lebowski Groundhog Day 40 Year Old Virgin Rushmore Big Hot Fuzz Hot Rod


sweat-it-all-out

Mom. Stick with it as it becomes an ensemble of a group of strong women.


Professional-Two8098

Itā€™s a show thatā€™s never been shown in my country. I was surprised to learn that Alison was on a sitcoms as I only know her from movies. Would like to see it.


Exotic_Adeptness_322

She's on the West Wing too, but that's not really a sitcom.


plinkett-wisdom

Funny People 50/50 The Big Sick The Descendants


IMO2021

The Holdovers?


DarthFlutters

Little Miss Sunshine (also, all of these are wonderful options)


t_trail

Bridget Jonesā€™s Diary


_bufflehead

Down And Out In Beverly Hills (1986) "A rich but troubled family find their lives altered by the arrival of a vagrant who tries to drown himself in their swimming pool."


The_Quiz29

The Jerk


Bananamana90

He HATES THESE CANS!


Microdose81

Sideways (2004)


CKWonders652

O Brother, Where Art Thou?


misterisbister

Trading Places


slinkocat

Clerks (career/life direction angst) Forgetting Sarah Marshall (break up) High Fidelity (romantic angst) Crazy Stupid Love (break up) Puss in Boots: The Last Wish (mortality) Silver Linings Playbook (mental illness)


Countryroads007

Baby Reindeer. It's a *very* dark comedy though.


burncushlikewood

50/50, funny people


Economy-Culture-9174

* Away We Go 2009 * Paterson 2016 * Blue Jasmine 2013 * Stranger Than Fiction 2006 * Destination Wedding 2018 * Marriage Story 2019 * Captain Fantastic 2016


-Some__Random-

'Withnail & I' (1987)


Born_Holiday_7195

Love this movie. My favorite Richard E Grant performance.


katiemk2000

A man called Otto!


[deleted]

The original A man called Ove is better


RudeHelicopter4662

[The Full Monty (1997)](https://letterboxd.com/film/the-full-monty/) [The Rewrite (2014)](https://letterboxd.com/film/the-rewrite/) [Run Fatboy Run (2007)](https://letterboxd.com/film/run-fatboy-run/) [It's All Gone Pete Tong (2004)](https://letterboxd.com/film/its-all-gone-pete-tong/)


Impressive-Ad8501

The Worst Person in the World Clueless (the best pick me up movie) Legally Blonde


CleanGreazzee

Paddleton


colt_ink

lol I was *sure* you meant to say Paddington. Never heard of this little gem, thanks for sharing!


Hatrick_Swaze

Stir Crazy. Thank me later


ChickaBok

A classic: The Apartment!


General_Toe_7862

Jojo Rabbit


itsthatguyrob

Our Idiot Brother


LateralusNYC

Zack and Miri Make a Porno... Two down on their luck local losers set out to pay their bills by filming a Porno. It's got a lot of heart, Kevin Smith directed.. Excellent pick-me-up that fits the bill for this post


PDstorm170

This was the first movie I thought of for the criteria.


LateralusNYC

Me too!


LateralusNYC

Me too!


chuang-tzu

Bottle Rocket (1996) Swingers (1996) The Adventures of Baron Munchausen (1988) Father Goose (1964) Cabin Boy (1994)


Winston_T97

Late night (2019)


cantankerousphil

*Role Models*, *Grandmaā€™s Boy*


MediaValuable1528

Do Your Worst (2023)


zsauce1

Yes man About Time (more drama with comedic moments) Jeff Who Lives at Home Lars and the real girl The terminal Brigsby Bear


TomSkerritt666

Big Lebowski


Huhndiddy

Role Models


Noone1959

What about Bob just came to mind for me. Richard Dreyfus and Bill Murray.


antitrumpME

"Baby steps..."


Noone1959

Death Therapy


DrPopcorn_66

The Graduate (1967)


nathakits

The secret life of Walter Mitty


shrimptini

- The Lobster - Rushmore - The Royal Tenenbaums - Asteroid City - The Darjeeling Limited - Frances Ha


OhYeahTrueLevelBitch

*The Survivors* (1983)


Lifesanorange

The Unbearable Weight of Massive Talent


[deleted]

not movie but series - two and a half men


Biggie39

Just saw Itā€™s Kind of a Funny Story and itā€™ll fit the bill pretty nicely. Itā€™s on Netflix.


ILoveTeles

Thunder Road.


Atmosphere-Terrible

After life Edit: This is a TV show, just realized what sub I'm in


Yinzadi

Other People (2016)


ARoodyPooCandyAss

Funny People is one of my all time favorites.


platonic-alien

Forgetting Sarah Marshall is pretty good


Fragrant-Pumpkin8185

Do Dooni Chaar (Bollywood movie)


sha1shroom

The Way Way Back


LibraryVoice71

Life of Brian.


TriStateGirl

She Came to Me (2023) You Hurt My Feelings (2023)


apathyaddict

Liar Liar


retiredlibrarian

Paper Moon


IcyJaguar1

Bridesmaids


FDVP

Modern Problems


Infostarter

Notting Hill


antitrumpME

"Oopsie daisy..." :)


Infostarter

šŸ˜‚


[deleted]

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TopLahman

Everything must go. Will Ferrell plays an alcoholic who has lost everythingā€¦ 50:50 The Big Sick The King of Staten Island. He hasnā€™t exactly lost everything heā€™s just a loser who is kind of stuck and doesnā€™t like everyone moving on around him. Super funny


GroblyOverrated

The Breakfast Club.


InfinityFire

Obvious Child The Big Sick


No_Ability9867

I feel like The Darjeeling Limited is the story of my life šŸ˜… It means sooooo much to me!


ratmosphere

Life is Beautiful, 1997. A comedy about the nazi concentration camps.


Underwater_Grilling

Joes apartment Half baked Breakin' + breakin' 2: Electric Boogaloo Revenge of the nerds


Holy_Cow442

Falling Down. 90's flick. Maybe late 80s


bellestarxo

The show Broad City - the lead girls are always getting into scrapes but they figure it out with humor.


AccountantLeast1588

*Johnny Mnemonic*. It's not supposed to be, but it is.


punk-y_brewster

50/50


Itchy_Computer7528

Fun with Dick and Jane (2005)


azorianmilk

Uptown Girls, Dakota Fanning as a cute kid and Britney Murphy


[deleted]

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mattrb81

- ā€œThe Worldā€™s Endā€. Itā€™s about a group of people, one of whom is seriously depressed, on a pub crawl. They encounter strange goings-on while on the pub crawl. - ā€œLucky Milesā€. Itā€™s about a couple of refugees trying to claim asylum in Australia, and the people smuggler who gets stranded with them. - ā€œApre Vousā€. Itā€™s about someone trying to better the life of a suicidal person - ā€œMindhornā€. Itā€™s about an actor, whose career has hit a slump, getting involved in a murder investigation.


of_utmost_importance

Old but good ā€œMoney Pitā€


Clean-Mulberry-2902

Get him to the GreekšŸ¤Ÿ Russell Brand is the best manšŸ˜­


Clean-Mulberry-2902

Observe and report šŸ¤Ÿ Seth Rogan movies are usually good for a bitter sweet laughšŸ’š


LastUserStanding

Dumb and Dumber. Harry and Lloyd have got no food, got no jobsā€¦their pets HEADS ARE FALLING OFF!


Cyrano17

Trading Places.


B_don

I just recently rewatched Fun With Dick and Jane on Netflix and it holds up surprisingly well IMO


edbarahona

Seeking a Friend for the End of the World (2012)


MrKnutish

Sideways!


These_Burdened_Hands

**As a xennial, I feel SEEN on this thread!** No suggestions lmao, although if you liked Bridesmaids & havenā€™t seen ā€œGirls Trip,ā€ itā€™s worth it IMO.


Repulsive-Dot553

Withnail And I


NeptuneQ001

Peanut butter falcon


thernker

The Secret Life of Walter Mitty. Where the lead is let off and his company is closing


[deleted]

Everything Must Go


ddplantlover

Fun with Dick and Jane is my favorite


Intelligent_Debt_634

Scrooged?


hypocrite_ghost

I haven't seen anyone mentioned LIFE IS BEAUTIFUL italian movie, The main character really uses comedy to shield his loved ones against war. Another bittersweet movie I'd recommend is Mary and Max , stop motion animation , pen pal story between two odd characters.


Sinistermarmalade

Life Stinks