Romantic Comedies by the Bay

By Erin Carlson

When it comes to rom-coms, New York City always seems to set the stage for meet-cutes, with the Empire State Building gleaming in the background. But if you left your heart in San Francisco, then you’ll need to add these unsung gems to your streaming queue.

Scenes from What’s Up, Doc? (1972); So I Married an Axe-Murderer (1993); The Five-Year Engagement (2012); illustrated by Iris Lei.

What’s Up, Doc? (1972): Barbra Streisand charms as endearing trouble magnet Judy Maxwell in Peter Bogdanovich’s screwball comedy, where she embarks on a love adventure with musicologist Dr. Howard Bannister (Ryan O’Neal) that hurtles the pair down Lombard Street in a high-speed Volkswagen Beetle chase. You’ll get a kick out of the scenes from San Francisco featuring Saints Peter and Paul Church, Chinatown and the Bay. When Bogdanovich was dreaming up the movie, he envisioned “something like Bringing Up Baby: daffy girl, square professor, everything works out all right.” The formula worked.

So I Married an Axe-Murderer (1993): The underrated Mike Myers romantic comedy flopped hard in the summer of ’93, making just $11 million at the box office, in drastic contrast to the $127 million success of competitor Sleepless in Seattle, the slick, unabashedly commercial blockbuster co-starring Tom Hanks and Meg Ryan. Like Myers, midway through his reign on Saturday Night Live, Axe-Murderer was wonderfully weird, capturing the City’s nonconformist zaniness. The actor portrays a North Beach beat poet who grows paranoid that his new paramour, a winsome butcher (Nancy Travis), is a serial killer.

The Five-Year Engagement (2012): This quiet charmer also underperformed in the theater, despite boasting two gifted rom-com actors: Emily Blunt, a master of comic timing, and Jason Segel, an oh-so-relatable goofball in the mold of the Judd Apatow male (sensitive and funny, with shades of Peter Pan syndrome). Nick Stoller directed the Apatow-produced Five-Year Engagement as a star vehicle for Segel. However, Blunt shines brightest. She’s a Ph.D. whose relationship with her fiancé (Segel), a sous chef, gets tested when a new job in Michigan uproots the couple from their happy life in San Francisco.

Scenes from Going the Distance (2010); Medicine for Melancholy (2008); The Wedding Planner (2001); illustrated by Iris Lei.

Going the Distance (2010): Echoing The Five-Year Engagement, two soulmates played by Drew Barrymore and her then-boyfriend Justin Long find themselves torn between love and career (a common millennial affliction!). A summer fling becomes serious when Erin and Garrett fall in love over six weeks in New York City. But, alas, her newspaper internship ends and she moves to San Francisco to work full time at the Chronicle. The lovers break up but later rekindle the flame when Garrett quits his job at a record company to manage a band in Los Angeles. (As one does.) This is one of the few rom-coms to end happily on the West Coast. Take that, When Harry Met Sally!

Medicine for Melancholy (2008): Seven years before winning an Oscar for Best Picture for his drama Moonlight, writer-director Barry Jenkins earned praise — and an Independent Spirit Award for Best Picture — with this romantic drama pairing Wyatt Cenac and Tracey Heggins as strangers whose Nob Hill one-night stand leads to hours spend walking and talking about the city, and includes a visit to the Museum of the African Diaspora. Their conversation topics: race, identity, gentrification. No, this is not a lighthearted comedy. But, like Richard Linklater’s Before Sunrise trilogy, there is joy to be found in watching two people get to know each other, surprising themselves along the way.

The Wedding Planner (2001): Released inJanuary ’01, one month before Jennifer Lopez and Sean “Diddy” Combs called it quits, this fizzy San Francisco–set romp marked Lopez’s first foray into mainstream romantic comedies. The Wedding Planner matched the luminous triple threat with peak aughts Matthew McConaughey. While the genre fit Lopez like a Versace dress, McConaughey seemed out of place, even though he looked the part. He plays Steve, a pediatrician engaged to be married who develops feelings for the woman planning his wedding. (Yes, that would be J.Lo!). Scenes were filmed in Golden Gate Park, San Francisco City Hall and the Filoli House and Gardens.

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