In 20 Years, Lost Weekend Built a Home in Miami Beach and Got Matt Damon Married

It’s only fitting that South Beach pool hall Lost Weekend, named for a 1945 Billy Wilder movie, has seen its fair share of random movie stars and celebrities. Like that one time Lenny Kravitz and Michael Stipe shot pool there. Or when Liv Tyler and Drew Barrymore sat at the bar for a drink.

But Lost Weekend’s brushes with fame began before the bar even opened 20 years ago. “Mickey Rourke used to own the space,” Lost Weekend co-owner Scott Frielich says. “It was called the Spot. Every time I tried to get in, I could never get past the door guy. Then, when we bought it, we ended up hiring the same door guy, Gilbert.”

"Nobody judges you here."

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Though, sadly, Gilbert passed away a few years ago, Lost Weekend is expecting plenty of old friends to show up for its 20-Year Anniversary Block Party this Saturday. Held on the block of Española Way between Washington and Collins Avenues, the block party will be a sensory overload. Attendees can expect burlesque dancers, drag queens, magicians, comedians, and lots and lots of live music. On an outdoor stage, a who’s who of local bands will perform, featuring everything from the funk of Spam Allstars to the electro beats of Afrobeta to the rockabilly of Key West’s Patrick & the Swayzees. “We’re expecting to see everyone come out of the woodwork,” Frielich says. “We’ve had so much loyal clientele over the years. They say marriage and kids are the worst thing for a bar, and divorce is the best, but for this party, we’re expecting everyone.”

There were a lot of memorable nights over the past two decades — far too many for Frielich to recall. But a few do come to mind. He remembers one night when then-MTV personality Carson Daly came in and was singing along to songs off the jukebox until 7 a.m. Another time, Frielich was thrilled to see Radiohead singer Thom Yorke hanging out at his establishment. As a Miami Heat fan, Frielich was especially proud to host and officiate a pool tournament with the local basketball team. “It was back in ’99. Pat Riley was the coach, and he gave me a thousand dollars to give to the winner. The finals involved Tim Hardaway and Dan Majerle. They took it so seriously. They each brought their own cue stick and were fighting and cursing about every shot.”
Frielich says he was also present when one of the world’s biggest movie stars found love. “They filmed the movie Stuck on You here with Matt Damon and Greg Kinnear as Siamese twins. Matt would stick around and shoot pool after shooting. One night afterwards, we took him to Crobar. He liked one of the bartenders and got her phone number. He ended up marrying her, and she is still his wife to this day.”

But the people who run Lost Weekend say it isn’t the occasional celebrity dropping by that has helped them survive two decades, which might as well be an eternity in South Beach years. “We’ve stuck around because we have no pretension,” general manager Travis Carey says. “People come in straight from the beach dressed in shorts and flip-flops and end up hobnobbing with women in gowns headed out to the clubs.”

After the party, Lost Weekend will look toward the future, where it hopes to reestablish itself in West Palm Beach — where the first Lost Weekend started in ’94 — with a planned opening by the end of 2016. But Saturday night will be all about South Beach. “This is a place where locals know they’ll always be taken care of,” Carey says. “Nobody judges you here.”

Lost Weekend 20 Year Anniversary Block Party, with Spam Allstars, Afrobeta, and others. 2 p.m. Saturday, October 1, at Lost Weekend, 218 Española Way, Miami Beach; 305- 672-1707; facebook.com/LostWeekendSB. Admission is free.