The Harvard Sailing Team hit it big on YouTube when YouTube was first hitting it big. The New York-based sketch group—which is unrelated to the university or sailing, as the troupe's fine print reads—began uploading short, simple sketches to the Internet in 2007 and was among the first to realize the site's comedic potential. Videos like "Boys Will /be Girls" and "Hipster Thanksgiving" went viral, and the team's nine members (Jen Curran, Clayton Early, Faryn Einhorn, Katie Larsen, Adam Lustick, Billy Scafuri, Chris Smith, Rebecca Delgado Smith, and Sara Taylor) have since hit "that guy from that thing" level in Hollywood, while continuing to produce satirical videos with improving production values.
Before the Web fame, the group found its collective comedic voice on the stage of the People's Improv Theater. And to this day the members are at their best as live performers, always gussied up in their signature argyle sweaters. The large group (enormous by comedy standards) has been working together for nearly a decade and as such has the ability to create a stream of changing dynamics as each member effortlessly plays off the others, riffing on topics that range from gender norms to pop culture to nonsensical anything. Along with jokes, the members channel their theater backgrounds and weave in song and dance for a fun, multifaceted approach to sketch comedy.