Episode: “Opening Night” (Season 4, Episode 10)
Address: 303 West 48th St., New York
Website: sombrerorestaurant.com

While in NYC to play Max Bialystock in The Producers, Larry is urged by Jeff to cash in on his anniversary gift from Cheryl (a free pass to sleep with one woman of his choice) before it expires. Against his better judgment, he ditches his line memorizing to meet Jeff and his new lady friend, Christina, who reveals to the two that she's a fellatio instructor. After Jeff conveniently disappears, Larry and Christina head over to this Mexican restaurant (which has since been reincarnated as “Sombrero”) in Hell's Kitchen, where Larry's blows his chances by drowning his taco salad in hot sauce when Christina mentions that it makes a man's spunk taste “delicious.” The result? He makes himself—and his date—completely sick.