Notting Hill
1999 was the year that brought us this masterpiece of the rom-com genre. Starring Julia Roberts as basically herself and Hugh Grant as the unsuspecting book shop owner who falls in love with a movie star, this movie not only covers fall, but all the other seasons, too. This reporter has a confession to make: Notting Hill is my favorite movie of all time and I watch it multiple times a year, but fall is an especially good time because it’s just so cozy and comforting. It also has a great soundtrack, including Ain’t No Sunshine by Bill Withers, She by Elvis Costello, Al Green’s cover of The Bee Gees’ How Can You Mend a Broken Heart, and Gimme Some Lovin’ by The Spencer Davis Group. Watch this if you love streets with pastel-colored buildings and dry British humor.
You’ve Got Mail
This list would not be complete without a Tom Hanks rom-com. This one co-stars Meg Ryan as another book shop owner, just like Hugh Grant in Notting Hill! What’s better than book shops in autumn? Set in New York City, You’ve Got Mail (1998) follows the aforementioned owner of a small, independent book store (Ryan) and the big-business owner of a Barnes and Noble-esque chain (Hanks) who threatens to put the former out of business. Watch if you love the enemies-to-lovers trope and cozy-maximalist apartment interiors.
Remember the Titans
You can’t have fall without football season. And what better football movie to watch than Remember the Titans? Starring Denzel Washington as a football coach who comes to a new high school where football is everything and Cuba Gooding Jr. and a very young Ryan Gosling as two of the players, this 2000 sports drama is a great feel-good movie to watch with the whole family.
Midnight in the Garden of Good and Evil
Based on the incredible novel John Berendt, this 1997 movie stars Joan Cusack, Jude Law, and Kevin Spacey. If you can stomach that last actor, then this is a great murder mystery full of ghosts and character actors galore. It follows a journalist who comes to Savannah to write an article about a Christmas party and ends up staying to cover an unfolding murder case. Watch if you like spooky Southern movies.
St. Elmo’s Fire
Speaking of The Breakfast Club, a lot of that cast overlaps in St.Elmo’s Fire. Both came out in 1985, but instead of a group of high schoolers, St. Elmo’s Fire follows seven college best friends who go to Georgetown University. Starring Emilio Estevez, Rob Lowe, Judd Nelson, Ally Sheedy, and Demi Moore, this Joel Schumacher rom-dram is one Brat Pack movie you don’t want to miss. Watch if you like good-looking people and the ’80s aesthetic.
The Haunted Mansion
I would be remiss if I didn’t include my favorite Eddie Murphy movie, 2003’s The Haunted Mansion. It follows a real estate agent (Murphy) who takes his family on a vacation at the behest of his wife (Marsha Thomason) — but on the way, they stop at a mansion he’s been asked to sell. There, they meet a whole lot of ghosts who need help breaking a curse. Watch it now, before the new Haunted Mansion remake comes out next year! The 2003 version is a great autumn movie for kids. I loved it when I was a kid myself — especially the love story. Oh, and the crystal ball lady. She’s the best. Watch if you like spooky, but not too spooky.
Autumn in New York
Okay, the Tomatometer on this one is a shockingly-low 19%, but having recently watched this myself for the first time, I would say to ignore the critics on this one. If you like late ’90s and early 2000s romantic comedies, there’s a very high chance you will like this movie. Sure, it’s sappy. But isn’t that the point? It stars Richard Gere as an Anthony Bourdain-esque, grey-haired bad boy chef who decides he’d like to date the daughter of one of his old friends who is less than half his age. Who better to play this early prototype of a manic pixie dream girl than Winona Ryder? Anyway, I’ll be honest: Richard Gere’s presence alone was enough to convince me to watch this movie. But the fact that it’s set in New York City and has some absolutely amazing autumn walk-through-the-park moments when the leaves are all orange and gold really put this one over the edge for me. I enjoyed this movie very much and would even go so far as to say that I would see it a second time if the opportunity presented itself. Watch if you like romantic comedies regardless of the plot’s plausibility. Oh, and while you’re at it, listen to the song of the same name by Ella Fitzgerald and Louis Armstrong.
Runaway Bride
Okay, now that the cat’s out of the bag about how much I love Richard Gere, here’s a 1999 Gere movie that I love so much, I could see myself getting into a spirited debate with someone at a party if started trash-talking it. I’ve probably seen Runaway Bride a minimum of 10 times and I have no intention of stopping anytime soon. Set in the quaint, made-up town of Hale, Maryland (it has taken me years to understand that pun), the autumn vibes are strong in this movie. Gere plays Ike Graham, a pithy New York columnist who gets fired after small-town engagement-repeater Maggie Carpenter sends his editor (Rita Wilson) a list of factual errors in his article all about her proclivity for leaving men at the altar. In an effort to restore his journalistic credibility, Graham follows her to her hometown in order to write a story about who she really is — but he soon finds himself a little too close to his subject. Watch if you like good movies.
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