Movies to Watch Over and Over Again
And how (and why) to make a list of your own
Note: reminder to my loyal readers that this is part of my freelance writing class with the magnificent Amber Petty. This week’s assignment: write a list.
Life is hard! And for a lot of us, life has been extra hard lately! This list is a suggestion. It’s a practice; it’s a way of life. Everyone, I believe, needs this list. You need to know the movies that you can watch over and over again and never get tired of, because someday, you’ll need it. When times are tough, you’re drained, and you do not have the capacity to cross your fingers through something you hope will be entertaining and not leave you any space to think about your own troubles. You need to enter a movie theater of the mind: dark and exciting, enveloping, memorable. This list will be deeply personal to the individual. Some of the movies in my list below are dark, or depressing, or frightening, or not good, and the ones in your list might be those things too. Your Over and Over Again Movies (or OOAMs, let’s call them) need to scratch itches for you that not everyone will understand, but it’s ok. The reasoning behind your OOAMs need not make sense or please the masses. The only criteria for an OOAM: they need to be watchable, for you, over and over again. That’s it. Let me show you what I mean.
Can a movie become an OOAM for as mundane a reason as “because it’s on TV all the time?” Yup. Goodfellas also happens to be an outstanding and rigorously entertaining movie that a lot of people love, but if you find yourself craving French Kiss or Grease or Office Space (off the top of my head), it’s because, sometimes, TV programmers know what they’re doing. Goodfellas will always captivate me because it feels long, in a good way (if you’re watching it on TV, you’re making an afternoon of it); a lot of things happen in it, and whenever I watch it I find myself thinking, “Oh wow, we’re not even at that part I love yet.” When I want to feel enveloped in a movie and taken away from life, I like being able to stare down a long road and know that there’s a lot of good stuff in store. KAREN!!
Men in Black (1997)
Not getting too esoteric yet here at the beginning of my list: Men in Black is light and fun and funny, and I’m really serious when I say that Vincent D’Onofrio’s inspired performance as a cockroach alien wearing a human man as an ill-fitting suit is one of the greatest of our time.
Now we’re getting into it. If you suggest this over-two-hour story of Mozart’s rivalry with lesser composer Salieri to a bunch of people who are over for brunch, not everyone’s going to be into it. But I love a serious movie with genuinely funny parts (shoutout to Jeffrey Jones as the dimwitted emperor Joseph II). I also see Amadeus as a unicorn: it’s a movie based on a play that doesn’t feel stagnant, like, well, a filmed version of a play; instead, Milos Forman’s adaptation brings the writing to life in a glorious celebration of music and period costumes. Bonus: a very, very young Cynthia Nixon as a timid, frightened housemaid. Miranda would never!
Prestige aliens really do it for me. I’m not a sci-fi person, generally, but that makes serious, well-made alien movies stand out. There’s something exciting about a subject you’re not usually interested in done in a new way. I would call Arrival a feel-good movie: it’s about problem-solving and acceptance and the love of learning. This movie is quiet and a little spooky and goes down real smooth, as any OOAM should. Here’s a tell: if a movie has a twist or a surprise ending, and it makes you feel tingly even after you’ve seen it three hundred times and know what’s coming, you’re probably looking at an OOAM.
Make that prestige aliens with a strong female lead. Can your OOAM be rooted in nostalgia? You know the answer by now: of course it can. My mother read something about Contact when it came out that made her hesitant to let me see it at age twelve (I can’t imagine what it was, Contact is pretty family-friendly), but she caved and we saw it in the theater together. I found Jodie Foster captivating as a passionate diehard science lady (putting it in terms I would have used at the time), perhaps another nostalgia leftover from one of my early childhood OOAMs, the 1976 Freaky Friday, starring a 14-year-old Foster.
Angels in America, HBO six-part series (2003)
Your OOAM can be depressing! It can! You can escape the horrible world by going into another one. R.W. Fassbinder said, “Art is sad so that we don’t have to be.” I think about that all the time. And at the end of the day, if something’s really good, it almost doesn’t matter what it’s about. HBO pulled out all the stops for its production of Tony Kushner’s masterpiece about the AIDS crisis, mainly through its casting: Meryl Streep, Jeffrey Wright, Mary Louise Parker, Emma Thompson, and Al Pacino as the monster Roy Cohn as he’s dying, just gobbling up the scenery — who wouldn’t want to watch that over and over again?
Michael Clayton (2007)
Carry me away, prestige thriller! Take me in with your Tilda Swintons and George Clooneys, your fables of corruption and morality, against a grim New York backdrop and a thumping soundtrack! Give me a British actor doing that adorable British actor American accent as a brilliant litigator losing his grip on reality! Win many awards for it and inspire prestige television (read: Succession)!
A Serious Man (2009)
When I talk about a movie theater of the mind, I’m talking about the Coen brothers. They’re a perfect microcosm of how personal each person’s OOAMs are — everyone has a different favorite Coen brothers movie, and a few that they hate. People I know and love hate A Serious Man. To me, it’s the perfect delicious sweet spot of creepy and hilarious that makes the Coen brothers who they are. I love how we’re dropped into an extremely specific universe (the predominantly Jewish suburbs of the Twin Cities in the 1960s) and led by the hand through a typically Coenian adventure of “one day a man is minding his business when some bizarre and frightening people start yelling at him and his entire life breaks down.” In a nice bit of synchronicity, this film is very personal to the Coen brothers, too, supposedly based on their father. Maybe that extra layer of weirdness that can only come from the specificity of real life is what makes this one tough to take for some people, but I knew the first time I saw this in the theater that this one was going to make my list.
Sunset Boulevard (1950)
If you’re one of those people who doesn’t do black-and-white movies, I get it, I get that it’s more of an undertaking, but also, no. Old movies can be perfect OOAMs, the ideal cocktail of comfort and entertainment. This was the beginning of the era of film, and everyone involved was PSYCHED to make something big and dramatic and glittery and awesome, so take advantage of that. Find one that makes you laugh and hang off the edge of your seat so much you’ll forget you’re watching an old movie — with Gloria Swanson’s performance as the crazed, delusional former movie star Norma Desmond, which deserves the word “iconic” more than anything else that’s had that ubiquitous term thrown at it, Sunset Boulevard gets my vote.
Waiting for Guffman (1996)
Yes, your OOAM list will be dotted with bizarre dark choices that no one but you will understand, but you’re also gonna need some stuff that makes you laugh. Waiting for Guffman is the first of Christopher Guest’s signature mockumentaries; when I saw it as a teenager, I could not believe the genius of the idea, and how hilarious these very real small-town characters were. Guest’s traditional ensemble — Catherine O’Hara, Eugene Levy, Parker Posey, Fred Willard, Guest himself, and tons of other comic actors you’ll know and love in smaller roles — are pitch-perfect as sweet, naive aspiring actors who believe the pageant they’ve mounted about the history of their small Missouri town is destined for Broadway. Guest’s two other mockumentaries, Best in Show and A Mighty Wind, which dive into competitive dog shows and the folk music scene, respectively, are also superb.
Are you getting the idea? Think about the movies that envelop you like a big squeezy hug and hold you there from beginning to end, and you’ve got your list. Don’t worry about what won an Oscar and the movies you pretend to love to sound impressive; if you have a craving for something with a 20% on Rotten Tomatoes more than once a year, that’s an OOAM. Be proud of it. The above are only highlights from my list; below, for reference, are the rest of my OOAMs, so you can really drink in the weirdness and feel inspired to start on your own list. Happy watching!
My Complete List of Over and Over Again Movies
In addition to the above:
It’s a Wonderful Life (1946)
Back to the Future trilogy (1985–1990)
With a Friend Like Harry (Harry, Un Ami Qui Vous Veut Du Bien) (2000)
A.I. Artificial Intelligence (2001) (Warning: this movie is bad)
When Harry Met Sally… (1989)
The Prestige (2006)
Being John Malkovich (1999)
Midnight in the Garden of Good and Evil (1997)
The Truman Show (1998)
All Harry Potter movies (2001–2011)