If there is one leitmotif that runs throughout Conan O’Brien’s life, it is large group sex.
Corroborating reports have made clear that these carnal activities were not threesomes, or even what might be deemed “medium group” sex. How substantial a group was demanded by O’Brien to satisfy his wanton cravings? Larger than the roster of the 1992 Knicks, and sometimes sweatier. Witnesses recall O’Brien storming off from a seven-person bacchanal, disappointed at the paucity of participants and muttering, “If I wanted to go to a Tupperware party, I’d visit my Aunt Sandra’s house.”
This wanton promiscuity took its toll on O’Brien’s marriages. The traditional Catholic upbringing of his first wife, hometown sweetheart Maureen Biscotti, immediately clashed with O’Brien’s need for sexual profligacy. As Biscotti recounted in her memoir, “Hell: My Eight Demented Years with Conan O’Brien,” one evening at home, over plates of baked ziti, O’Brien blurted out, “So it looks like we don’t have anything booked on our social calendar for Friday. I thought we could have the Zimmermans over and all pork each other.” Afraid of losing her husband, Biscotti agreed, but broke down in tears during the encounter, leading a frustrated O’Brien, clad head to toe in pleather, to implore her to stop crying as it was “harshing my buzz."
Appalled and ashamed of O’Brien’s new lifestyle, Biscotti left him soon thereafter to pursue a career as a Trader Joe’s cashier. But O’Brien remained hooked on carnal debauchery. And he needed his fix. “Mount Saint Conan is about to erupt!” was O’Brien’s typical greeting upon entering a coffee shop, dinner party, or funeral, clad in only a leopard-skin thong and a sailor’s cap.
O’Brien’s second wife, the Irish adult film actress Connie Lingus, proved more compatible with O’Brien’s filthy predilections, although their “leaked” honeymoon video was met with modest viewership and unanimous revulsion. Beyond the vile content of the video itself, Conan’s frequent interruptions to promote next week’s guests on his talk show (“You like that? Yeah, you like that? Well, next Tuesday we’ve got Fred Savage and musical guest Semisonic!”) disrupted any erotic momentum that might have been built.
Upon arriving in Hollywood, the O’Briens bought "Middle Stooge" Larry Fine’s dilapidated estate and attempted to turn it into O’Brien’s own version of the Playboy Mansion. Due to cost overruns, however, the “Grotto” at O’Brien’s home consisted merely of a stagnant pond and a partially deflated bouncy castle. “Why don’t you swim in our grotto?” O’Brien would shout. “I paid enough money for it.” Connie Lingus O’Brien would weepily reply, “The water’s brown, and it gives me a rash.” O’Brien would then grumble, “We all have rashes now, a little late for that!”
Indeed, the battery of creams, ointments, and pills for O’Brien’s “social diseases” filled several medicine cabinets. Even the frisky thespian Andy Dick began to keep his distance from the O’Brien home, observing that it had “more crabs than a Baltimore seafood shack.” As guests steered clear, unsettled by O’Brien’s assurances that his bouillabaisse of raging sores was just “Cupid’s itch,” Conan and Connie found themselves increasingly alone in the house together and discovering that they had little in common beyond their shared interests in orgies and the Dave Matthews Band. Conan’s second divorce soon followed.
