Conan O'Brien broke new ground on Conan last night — only it was rather inadvertent. O'Brien opened Monday night's episode — a special featuring the cast of Orange is the New Black — with a sketch in which his famous red coif was touched up by interim hairdresser, Sophia, AKA Laverne Cox. Though she does strongly recommend that O'Brien change his horrifying clown hair, Cox does give him some props: "You know Coco, I really do admire you… You really are an inspiration — the very first transgender talk show host."
Despite Conan insisting he's a man, Cox remains unswayed, pointing out, "Your voice is higher than mine! You're telling me you're not transitioning?" As for the final verdict on his hair, Andy Richter shows up in a socket-fried red wig and busts out his best Galina "Red" Reznikov to deliver the bad news to Coco: "You look absolutely ridiculous."
Elsewhere on the episode, Uzo Aduba revealed her conservative mother's surprisingly favorite OITNB scene — the one where Piper beats up Pennsatucky — and teaches O'Brien how to make her patented crazy eyes. Aduba's secret: "Make your eyes really big and think about something that you love." O'Brien struggles with it at first saying, "When I think about something sexy and erotic, I just look like a narrow-eyed creep!" The cross-eyed glare O'Brien eventually comes up with, though, is pretty harrowing.
The rest of Conan's Orange is the New Black-themed episode featured numerous highlights, including O'Brien's absurd spin on the show's opening credits; Cox talking about the rising voice of the transgender community and the time her twin brother got mistaken for her (a musician, he was upset only because someone thought he was an actor); and Lea DeLaria's graphic, yet informative, tips to Natasha Lyonne on how to have lesbian sex.
Kate Mulgrew also got the chance to dish out some ice cold revenge, peering into the depths of O'Brien's soul and reminding the host that he nearly ruined her career 15 years prior when he made her do an Irish jig on his show. His punishment: Another outlandish dance, though as O'Brien noted, "It's not really revenge if that's the crap I'm doing all the time on this show anyway!"
Check out those clips below, and more from the Orange is the New Black extravaganza over at Team Coco.