June 2-4, Civic Center Plaza & Bill Graham Civic Auditorium, clusterfest.com
Holy mother of God. The lineup for the inaugural Colossal Clusterfest — a new co-production between Outside Lands producers Another Planet Entertainment and Superfly — is unlike anything this city has seen. From industry heavyweights like Jerry Seinfeld and Kevin Hart to rising favorites like Hannibal Buress and the ladies of Broad City, this three-day festival is a comedy fan’s dream. Colossal Clusterfest will also have tunes courtesy of Ice Cube, Tegan & Sara, and Princess, SNL alum Maya Rudolph’s badass Prince tribute groups. Make sure you don’t sleep on the bottom of this bill either, where you’ll find highlights like Chris Gethard doing a live taping of his superb podcast, Beautiful Anonymous, stand-up from Rory Scovel and James Adomian, and the quartet of Alaska, Bob, Ginger, and JuJubee representing for the funny ladies of drag.
April 20-22, at Cobb’s Comedy Club, cobbscomedy.com
If you’re the type of person who moans audibly when a comic goes blue, you might not want a piece of Anthony Jeselnik. The comedian — who gained notoriety for his savage takedowns of C-list celebrities like Charlie Sheen and Donald Trump on several Comedy Central roasts — has made a name for himself as a performer who’s quick to offend but who ultimately has a salient point bubbling under his harshest lines. Given the state of affairs today, one has to wonder how Jeselnik will find time to take aim at the myriad of juicy targets in his sights. Strap in and get ready.
April 24, 7 p.m., at the Jewish Community Center of San Francisco, jccsf.org
Even if you don’t know character actor Stephen Tobolowsky, you know him. He’s slid under the radar as Ned Ryerson in Groundhog Day, Sammy Jenkis in Memento, and as an actor in countless other roles. In his life beyond the screen, Tobolowsky has also created one of the more compelling, masterful podcasts out there today with The Tobolowsky Files, which pivots from personal stories and Hollywood anecdotes to more profound discussions of life’s intangibles. Hearing him live is always amazing, so once you finish re-watching Groundhog Day, make sure you find your way to the JCCSF for what will surely be a memorable evening.
May 17-20, at Oasis, sfoasis.com
While drag queen Trixie Mattel may not have won her season of RuPaul’s Drag Race, the Barbie doll-painted clown has enjoyed immense success since competing on the show. Not only is Trixie more than happy to break the speed limit to go there on any taboo topic, she is hysterical, charming, warm — and, most impressively, a sight to behold. Performing under the welcoming auspices of Heklina and D’Arcy Drollinger’s SoMa club, Oasis, Trixie will offer fans four chances to take her out of the plastic and get a full dose of one of the most original queens to ever “sashay away” from Miss Ru.
ID10T Music Festival & Comic Carnival
June 24-25, Shoreline Amphitheatre, id10t.com
If you can have one ridiculous comedy festival in San Francisco this spring, why not two? ID10T is the brainchild of Chris Hardwick, the comic best known for hosting AMC’s Talking Dead and Comedy Central’s @midnight, and for creating the Nerdist empire. His two-day affair mixes comedy with music, as stand-up Demetri Martin, SNL news desk co-anchor Michael Che, and Bob’s Burgers voice talent Dan Mintz compete with the likes of Weezer, Girl Talk, Animal Collective, and Car Seat Headrest for your attention. Make sure not to miss Riki Lindhome and Kate Miccuci in their musical hybrid act, Garfunkel & Oates, whose discography features classics like “Pregnant Women are Smug.”
August 2 – 5, The Masonic
OK, we’re going to cheat a little here, because where Ali Wong is concerned, it’s almost necessary. Wong grew up in San Francisco and performed at many venues in the city before moving to New York. Last year, her debut comedy special, Baby Cobra, premiered on Netflix. Filmed in September 2015, when Wong was seven months pregnant, the hour-long set propelled her to stardom. A handful of dates announced for last December at Cobb’s sold out in seconds and led to a secondary ticket market that rivaled San Francisco’s newly-arrived Hamilton in its mark-up absurdity. This is all to say that if you want to see Wong — and trust us, you do — you’d best grab a seat for one of her August shows at the Masonic, ASAP.
Check out more from our Spring Arts Guide here: