Haven’t given it a lot of thought, but two that come to mind are “Flashdance” and “Risky Business”
“Elf.” I even watch it in the summer when I need a good laugh.
Dirty Dancing
Groundhogs day
Lots of Xmas movies
Strange Brew is the Citizen Kane of guilty pleasure movies.
Green Card. I don’t know why but I love that movie. Joe vs. the Volcano. Wayne’s World.
Mr. loves Mamma Mia… I want to scream “Mamma mia!!!” and run out of the room. Although I have to say that rsome choreography is quite creative, especially the scene with dudes in flippers dancing. If you have ever tried walking in flippers, you will understand. 
Our guilty pleasures are Pixar movies. The Incredibles, Toy Story movies, etc. Two adults watching a kid movie? Definitely along the lines of guilty pleasures.
Galaxy Quest.
You’ve Got Mail. And it isn’t a movie, but I can watch West Wing reruns forever. Josh Molina (Will Bailey) has just started a podcast where he is parsing every single episode (the podcast is longer than the episode itself each time ). And I am happily rewatching, then listening to his podcast.
Watching the second lord of the rings movie and skipping all the parts with Sam and Frodo.
Thanks for the tip about The West Wing Weekly podcast, @intparent! I miss West Wing.
Streaming on Netflix! (Although I own the full set on DVDs, it is the only DVD series i have).
Love UP and also Inside Out. On the airplane when I just need to be happier, I like watching Pixar and other kid movies. They’re a great way to pass the time.
Bring It On
Fairly new, but I have watched it 2X. Brooklyn.
50 First Dates. Love Drew Barrymore and its such a heartwarming, while still being comical, movie
The Big Chill
St. Elmo’s Fire
Grease
Splash
The Parent Trap. Lindsay Lohan version. I sometimes catch my H watching it and sniffing through tears a bit!
Movies that I can watch again and again:
Love Actually
Up in the Air - George Clooney
Dirty Dancing
Sex and the City - the first movie
Pretty in Pink
Sixteen Candles
Titanic
Love Actually
Apollo 13
The Graduate
Guess Who’s Coming to Dinner
Miracle on 34th Street
Not sure what makes it a guilty pleasure though. Just the ones I’ve watched a dozen times
Love Actually
The Family Stone
Under the Tuscan Sun
Soul Food
Ferris Bueller’s Day Off
The Godfather