Beginner’s Guide to 90s Rom-Coms

While You Were Sleeping

Year: 1995
Directed by: Jon Turteltaub

Along with Julia Roberts, Sandra Bullock dominated the movies in the 1990s. She was the brunette, Roberts the red-head and Meg Ryan (whose film will come soon) was the blonde. Bullock tried her hand at everything from action flicks to thrillers to period dramas and back again.

My favorite of her film’s is this Christmastime gem featuring a stellar ensemble including Bill Pullman (again!), Jack Warden, Peter Boyle, Peter Gallagher and Glynis Johns. Bullock plays Lucy, a token collector for the Chicago Transit Agency who has a secret crush on Peter (Gallagher), who visits her booth daily. On Christmas day he gets mugged, falls on the tracks and she saves his life.

After a misunderstanding at the hospital, his family comes to believe that Lucy is Peter’s fiancée. This is all well and good until his brother Jack (Pullman) shows up and Lucy begins to fall for him instead.

Check it out on MUBI | Like it? Buy it on Amazon.com

My Best Friend’s Wedding

Year: 1997
Directed by: P. J. Hogan

Note: Before I delve into this film, I have to mention another 1994 rom-com also directed by P. J. Hogan — Muriel’s Wedding. ABBA and Toni Collette fans alike will love that movie to death.

That said, this film is one of my favorites ever. I can — and do — often quote it (at the very least, every time I eat Jello-O or crème brûlée). Another wonderful ensemble, including Cameron Diaz, Dermot Mulroney and Rupert Everett (in what many believed at the time, and I still do, should have been an Oscar-nominated performance).

Roberts plays Jules, a food critic who is about to turn 28 years old. She once made a vow with her best friend Michael (Mulroney) that they would marry each other if they didn’t find the one by 28. She gets a call from him… telling her he’s met someone and he’s getting married. That someone is named Kimmy (Diaz), a 20-year-old college student and Chicago socialite. Shenanigans ensue when Jules heads to Chicago in an attempt to break up the wedding and convince Michael she’s been the one for him all along.

Check it out on MUBI | Like it? Buy it on Amazon.com

You’ve Got Mail

Year: 1998
Directed by: Nora Ephron

Which brings us to Meg Ryan. I am sure many of you expected to see 1993’s Sleepless in Seattle (also directed by Ephron and starring Hanks and Ryan) earlier on the list, but honestly I prefer this update of The Shop Around the Corner to that riff on An Affair to Remember.

Ryan and Tom Hanks really do have the most perfect chemistry together, and I think they are never better than they are in this film. Ryan plays Kathleen, the owner of a children’s bookshop who corresponds anonymously with someone via AOL Mail. This turns out to be Joe Fox, the owner of a mega bookstore chain (one with coffee and bargain prices like Barnes and Noble). As always, shenanigans ensue as the audience knows who Fox is and Fox knows who Kathleen is, but Kathleen remains out of the loop as she tries to save her beloved bookshop.

Again, this film doesn’t just have two great leads, but is also had a great ensemble cast, including Greg Kinnear, Jean Stapleton, Steve Zahn, Dave Chappelle and Parker Posey. It also remains one of the best time capsules of late-90s internet culture (much like the Sandra Bullock thriller The Net from a few years earlier). If you ever miss the charm of dial-up, you are an idiot, but you can pop this film in and hear that awful/wonderful music of the gone, but never forgotten dial-up modem.

Check it out on MUBI | Like it? Buy it on Amazon.com

Blast from the Past

Year: 1999
Directed by: Hugh Wilson

Sometimes I feel like no one saw these last two films but me and my family. They are both great films. This first one came out just before Brendan Fraser’s major breakout film The Mummy, and features him in what I think is his most charming and constructed performance. It’s also one of the last films to feature Alicia Silverstone in a lead role post-Clueless.

Fraser plays Adam, whose parents — Calvin and Helen (Christopher Walken, Sissy Spacek) — moved into a bomb shelter under their house after they mistook a cashing airplane for a nuke during the Cuban Missile Crisis. Helen is pregnant and Calvin set the lock on their shelter to not open for 35 years, “for their protection.” Thus, Adam has never known anyone other than his parents and all he knows about the world and pop culture comes from the old episodes of television they watch via a kinescope and the records his father stored up.

When the lock opens, 35-year-old Adam heads out into modern-day Los Angeles to get some supplies (his father is convinced everyone is mutants from the nuclear blast) so they can continue to live in the shelter. While above ground he meets Eve (Silverstone) and falls for her immediately. The rest of the movie is a fun fish-out-of-water/will-boy-get-girl story, that is sharp enough that its schtick never gets old.

Check it out on MUBI | Like it? Buy it on Amazon.com

The Bachelor

Year: 1999
Directed by: Gary Sinyor

Really though, I don’t think anyone has seen this movie but my family. We all have our own copies of it on DVD. Memories of one Christmas where people fought over a copy of it will go down in our family lore for generations. It is so damn funny. Like You’ve Got Mail, it is a modern take on a classic film, this time the Buster Keaton classic, Seven Chances.

Chris O’Donnell is Jimmy, who must get married before his 30th birthday — which is in two days — in order to inherit his grandfather’s estate. Also, if he doesn’t inherit the estate, his grandfather’s billiard company will be shut down and thousands of employees will lose their jobs. Jimmy asks his long-time girlfriend Anne (Renée Zellweger) to marry him, but he does it so poorly (no, really, it is the worst proposal ever) that she heads off on a trip with her sister Natalie (Marley Shelton). It is so bad, his grandfather (a brilliant turn from two-time Academy Award winner Peter Ustinov) dies when he hears about it.

Jimmy then turns to a series of ex-girlfriends (including Mariah Carey, Sarah Silverman, Jennifer Esposito and Brooke Shields) to marry him. Artie Lang, Ed Asner and Hal Holbrook are a hoot as his friends and business partners who try to help him in what seems to be an impossible task, while James Cromwell steals the show as the gloomy priest they bring along everywhere. The final sequence, which culminates in several thousand brides in gowns chasing Jimmy, remains one of the best uses of San Francisco’s hills to this day.

Check it out on MUBI | Like it? Buy it on Amazon.com

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Part of the Time Machine: Back to the 90′s Blogathon