MichaelIanBlackMichael Ian Black

Every year, Michael Ian Black, Michael Showalter, and David Wain — the pioneering comics behind the sketch ensemble Stella — make a promise that they’ll prepare diligently for their annual performance at SF Sketchfest.

Every year, those plans go to waste.

“The truth is, we always say that we can’t just go up there and wing it, because that’s unprofessional,” said Black. “But then every year, we always just go out and wing it.”

No one ever seems to protest the lack of planning for the Stella performances, and that’s because Black, Showalter, and Wain are masters of ad-libbing surreal comic situations. The trio shares a singular vision of comedy, and when one of them starts riffing on an inane topic, the other two finish in hilariously deadpan fashion.

On January 15, they’ll revive their Stella routine at Mezzanine, part of the 18-day epic that is SF Sketchfest — a collection of comedy events taking places in venues across the city.

As founding members of The State — the way-ahead-of-its-time sketch comedy show that aired on MTV in the early ’90s — Black, Showalter, and Wain started Stella in 1997, following the abandonment of their original project. With Stella seeing some underground success, they eventually landed that series on Comedy Central, although the show was also cut short by executives wary of its unconventional setups.

Stella sketches often take bizarre left turns that lead to ridiculous results. A jaunt to the local pizza joint somehow ends in a steamy orgy, and an innocent search for Santa Claus involves a grisly bit of cannibalism. No one is asked or expected to explain the strange twists — you just need to revel in its wacky, side-splitting absurdity.

The Stella performance at Mezzanine (also set to include musician Robyn Hitchcock) will be based on the trio’s “Nightclub Show,” a weekly comedy showcase they hosted during the troupe’s early days. Listen to one minute of Black and Showalter’s former podcast, “Topics,” — which is centered around off-the-cuff discussions of mundane issues that are also funny as hell — and you can get an understanding for how the Nightclub show will be uproarious without a single note being prepped.

“We’ve all known each other for so long,” said Black. “We’re at our most comfortable just fucking around with each other. We find that funny things usually arise from those kinds of conversations.”

The Stella Nightclub Show will be one of five acts that Black, a regular performer at Sketchfest, will take part in during the opening weekend of the festival.

“I never have any problem doing multiple shows at Sketchfest,” said Black. “It’s organized in a way that’s very friendly to the performers — focused on comedy, and not the industry. It’s basically a great way to catch up with friends and see great shows.”

Along with the Stella performance, Black will be hosting a version of his current podcast, “How to Be Amazing” with comedian Grace Helbig, and he’ll participate in two panels — one dedicated to classic music soundtracks of ‘80s movies, and another devoted to a debate on the merits of childhood versus adulthood. He’ll also take part in a live rendition of some of the best comedy bits from the McSweeney’s humor website.

It’s a crazy, hectic schedule for Black, but that’s nothing new for the 45-year-old comic. A versatile actor, writer, and touring comedian, Black first gained mainstream fame due to his ubiquitous appearances on VH1’s I Love The… series, which looked back on the various trends permeating American culture over the years.  Whether he was waxing poetically on the children’s book Where’s Waldo or ‘80s television show Eight is Enough, Black’s ridiculously dry takes on bygone phenomena always elicited laughs.

He parlayed the exposure from that show into a number of supporting roles in television and film, while also maintaining a steady beat on the stand-up circuit. He’ll be doing various standup gigs throughout this year, and, in some news that will surely please fans, he recently completed filming on the third version of Wet Hot American Summer, the 2001 cult classic movie that spawned an unexpected miniseries sequel last summer.

The latest version of Wet Hot American Summer will jump off 10 years after the events of the movie, which is set at a summer camp in the woods of Maine. That timeline makes slightly more sense than last year’s prequel, which amusingly featured a bevy of 40-something actors portraying teenagers. Black said the new series should arrive next summer, and, per tradition, will be largely unscripted.

That commitment to working without a safety net is what makes the work of Black and his cohorts so appealing. The Stella show on January 15 could be a disaster. It could also be legendary.

SF Sketchfest: Stella
January 15, 2017
7pm, $35 (21+)

A full schedule of SF Sketchfest events, including details on Black’s other appearances, can be found here.