Back in 1999 two upstart comedians, Rachel Dratch and Tina Fey, "accidentally" booked the same stage at Chicago's legendary Second City. So they decided to share the spotlight, performing their shows simultaneously: Dratch delivered a one-woman play about the obscure (possibly fictional) women's rights pioneer Edwina Garth Burnham; and Fey explored her sexuality in a series of monologues called, bluntly, "Cunt Poems."
The rapid-fire, mind-boggling sketch kicked off an installment of the pair's show, Dratch & Fey, which they performed at Second City, as well as the Upright Citizens Brigade in New York City. A clip of one such performance has blessedly made its way online, and despite the mediocre VHS quality, it captures Dratch and Fey's burgeoning brilliance at a unique moment in their careers: In 1999, Dratch was hired as a performer on Saturday Night Live, while Fey, after two years on staff, was named the show's first female head writer.
Dratch and Fey was directed by Jeff Richmond (he and Fey would later marry and work together on 30 Rock), and along with the duo's simultaneous theatrical productions, the show features a barrage of sketches that came from ideas they improvised during rehearsals, as well as a few of Fey's SNL skits that never made it to air.
Dratch and Fey would both go on to have strong tenures on Saturday Night Live, and the two briefly worked together on Fey's subsequent hit sitcom 30 Rock. Dratch was initially cast as Jenna in the show's pilot, but both Fey and NBC realized the actress did not fit the part and replaced her with Jane Krakowski.
"It was a failed experiment," Fey admitted to Rolling Stone, "because I took Dratch, who is inherently sweet, and said, ‘Let’s write her the opposite, have that cartoon-eyed person playing a diva and throwing fits,’ and it was one layer too many for what the show needed." Despite the tough break, Dratch played various characters in a number of 30 Rock episodes throughout the show's seven season run.