Today, the Upright Citizens Brigade is a bicoastal force and national comedy brand. But in 1999, when founding members Matt Besser, Amy Poehler, Matt Walsh, and Ian Roberts opened their first theater in a former strip club, nobody would have mistaken it for a landmark. The quartet opened the shabby dive as a haven for long-form improv; there, they performed their weekly Sunday night ASSSSCAT shows (joined by Saturday Night Live cast members and Late Night with Conan O’Brien writer/performers trying to stay in fighting improv shape) and taught a new generation of comedians their craft. Looking back on this era is like seeing the origin story of today’s TV comedy casts: People like Rob Corddry, Huebel and Riggle, Aziz Ansari, Aubrey Plaza, Ed Helms, and most of the Childrens Hospital/NTSF:SD:SUV/Burning Love teams all learned how to be funny here at the turn of the century.
Jason Spiro, then a photographer in his mid-twenties, became a fan of this rogue New York comedy scene right at the outset, and was enlisted by Matt Besser to take photos of the theater’s various ensembles (or “Harold” teams, after the Chicago-bred brand of long-form improv). From there, his cataloguing continued, and Spiro was able to be a corporate photographer by day and snap shots at night — capturing many familiar faces when they were young and wrestling for stage time just like everyone else, along with old pals from the UCB’s Chicago days such as Tina Fey, Rachel Dratch, and Horatio Sanz, who showed up to play. In honor of Vulture's Comedy Week, we had Spiro excavate some snapshots of some very familiar faces, taken during the 1999–2001 period. Enjoy.