Too many to list - essentially, just about any 50s/60s SF/horror film, 30s-50s Screwball comedies, Laurel & Hardy, The Three Stooges, The Little Rascals, 30s-50s swashbucklers, any adventure film with Errol Flynn, and dozens of random titles across the decades.

The Emperor’s New Groove. We quote it all the time and it’s very comforting to watch when we’re feeling bad.

Also, The Princess Bride and SpaceBalls.

Almost Famous
Heaven Can Wait
Superman : The Movie

Maybe just me but the movies I really like Empire Strikes Back, Superman 1 and 2, Scarface, Godfather 1 and 2, Taxi Driver, Cape Fear, and Back to the Future 1 and 2 I don't watch them a lot and maybe only until a new video format comes out DVD, Blu-ray, and 4K etc.

This is a surprisingly good movie.

Scent of a Woman

Nobody and the Deadpool movies are comfort for me as well.

Lately for me it's movies like Moneyball or The Big Short. The patter of the dialogue is very calming to me and they are fantastic films too.

I previously mentioned UHF so here's my new Comfort movie list.

UHF
Men at Work
Road House
Stone Cold
Don't tell Mom the Babysitter's Dead
Teen Wolf
Voyage of the Rock Aliens
Hot Dog the Movie
Miami Connection

I agree with Decker on Almost Famous, that's just a nice, warm blanket of a movie for me.

I have several, but the one that comes to mind first is...

Goodfellas

This is also pretty much my 'recommended for you' lineup on Tubi!

I could add Major League to that list too.

I was gonna add one but then I saw how old the thread was and realized I probably posted it already. So...ummm...never mind.

Scent of a Woman
True Romance
Planes Trains and Automobiles
Harold and Kumar's 3D Christmas
The Breakfast Club
Grosse Pointe Blank

Southern Comfort (1981)
The Favourite (2018)
The Comfort of Strangers (1990)
My Favorite Blonde (1942)
American Movie (1999)
Movie Movie (1978)

I bet you guys couldn't even see what I just did.

In the Heights

Looking back maybe we shouldn't have all replied with just images.

A lot of people's ideas of a comfort movie certainly are quite a bit different than mine.

A lot of good ones though. I'll add:

Big Fish
Marry Poppins
The Sound of Music
The Empire Strikes Back

Pretty much any 50's Sci-fi film. They can be good or bad....one of the very worst, The Astounding She-Monster, is one of the most comforting.

The Thomas Crown Affair (1999) is one of mine.

It's the suit, right? Guys dig the suit.

Swingers

Probably John Carpenter and Tim Burton's early work. And Arnold movies up until like, True Lies.

Whenever I want to feel good I usually watch the Star Wars OT theatrical cuts. Also, Serenity is one that I can put on at any time.

She's Out of My League is another big comfort movie to me. Its a perfect kind of movie that I can rewatch all the time.