“A Christmas Story” (1983)
Perhaps it’s because of the 24-hour marathon of the movie on TV every Christmas, but Bob Clark’s adaptation of the Jean Shepherd novel is a nostalgic look at the holidays and childhood that never gets old no matter how many times you watch it (even in one sitting during Christmas day).
“Back to the Future” (1985)
From the premise to the performances to the soundtrack, everything about Robert Zemeckis’ classic makes it a movie that you can never get tired of.
“Big” (1988)
The playfulness of Tom Hanks playing a teenager in an adult’s body is the essence of this movie and is a joy to watch even decades later.
“Caddyshack” (1980)
Watching the antics of these snobbish adults on a golf course just never gets old. And watching it recently, the jokes delivered by Rodney Dangerfield continue to suck you in. Bill Murray and Chevy Chase are amazing, but every line delivered by Dangerfield is solid gold.
“The Devil Wears Prada” (2006)
The style, the attitude — and that’s just Stanley Tucci in the movie! This look at the dirty side of the fashion business is always great to put on. Anne Hathaway and Emily Blunt are fantastic, but it’s, obviously, Meryl Streep as the taskmaster Anna Wintour doppelganger Miranda Priestly that is the movie’s heart.
“Dirty Dancing” (1987)
Whether it’s watching the movie to see Johnny (Patrick Swayze) and Baby (Jennifer Grey) fall in love or just to listen to its incredible soundtrack, this movie is always worth a watch.
“E.T. the Extra Terrestrial” (1982)
Steven Spielberg’s gift for childlike wonder is at it peak here in one of his most classic titles. Basically, when this movie is on you have to watch it until the end.
“Ferris Bueller’s Day Off” (1986)
John Hughes takes all the teen angst and wildness in his mind and bottles it into this extremely entertaining look at the dream skip day from school. How can you not watch this whenever possible?
“Fight Club” (1999)
David Fincher’s classic is required repeat viewing. Not just becuase Brad Pitt and Edward Norton are fantastic in it, but the little Easter eggs that are hidden throughout that give you hints of what’s really going on.
“Finding Nemo” (2003)
The Pixar classic is also one of the best animated movies of all time. There are countless things to love.
“Star Wars: The Force Awakens” (2015)
This is probably one of the most fun “Star Wars” movies to watch again and again. It’s fast start right into the action and its homages to the original trilogy make it very easy to get into.
“Hitch” (2005)
It’s the charm of Will Smith that is the backbone of this movie. There’s also the antics of Kevin James and the chemistry Smith has with Eva Mendes, but mostly it’s the movie star quality of Smith that keeps you coming back to this one.
“Friday” (1995)
The combination of Ice Cube’s talents both on the screen and cowriting the script, along with the out-of-nowhere casting of Chris Tucker, made this an instant classic. If you can’t get sucked into this movie two minutes into watching it something is wrong.
“Gladiator” (2000)
Ridley Scott made Russell Crowe an international superstar (and Oscar winner) in this swords-and-sandals epic. When you need a jolt of energy, this is the movie you can always turn to.
“The Godfather” (1972)
It’s one of the greatest movies of all time. You should probably watch it every single day.
“Goodfellas” (1990)
Martin Scorsese’s look at mob life is as funny as it is frightening. There is so much to enjoy about this movie you definitely need repeat viewings to fully appreciate it.
“Groundhog Day” (1993)
Honestly, how dare you if you’ve only seen this movie once. Bill Murray as a weatherman who repeats the same day is one of his best performances, and the crafting of the story by director Harold Ramis is a masterwork. See this movie as many times as possible.
“How to Lose a Guy in 10 Days” (2003)
The best movie from Mathew McConaughey’s rom-com era, this one should always be a consideration on a boring Friday night or when you’re procrastinating on getting work done around your place on a Sunday.
“Jaws” (1975)
It’s the movie that made Spielberg the toast of Hollywood and it’s always worth a watch.
“Mean Girls” (2004)
There have been many movies made about high school, but nearly none of them hit the right level of eerie accuracy and off-the-wall silliness of the experience like this one does.
“Memento” (2000)
This might be the most important movie on this list. 18 years after its release and I can still catch new things in this movie that I didn’t see the first dozen times watching it.
“The Notebook” (2004)
Find someone who looks at you the way Ryan Gosling and Rachel McAdams look at each other in this movie, and go and watch it for a weekend straight with them. You’re welcome.
“Office Space”
Mike Judge basically takes everything we hate about the real world and puts it into this movie. You can’t help but watch it whenever it’s on and wonder how Judge tapped into what you experience at work every day.
“Out of Sight” (1998)
Steven Soderbergh makes a classic crime caper and proves both George Clooney and Jennifer Lopez can be movie stars. Everything about this movie is done so well.
“The Princess Bride” (1987)
Rob Reiner’s classic love tale continues to delight decades after its release.
“Raiders of the Lost Ark” (1981)
It’s Spielberg again! Harrison Ford’s iconic archaeologist/adventurer character stars in this action masterpiece. So many movies since have tried to emulate what this has. That’s cool and all, but it never beats watching what sparked the inspiration.
“The Rock” (1996)
One of Michael Bay’s least infuriating movies, Sean Connery and Nicolas Cage are great and the action in the movie never gets to “Transformers”-level craziness. And there’s actually a good plot!
