Neil Patrick Harris and the entire SNL cast perform the theme to Doogie Howser, M.D.. Harris wears a tuxedo while everyone else is dressed as Doogie Howser in blonde wigs, lab coats with a picture ID of Doogie on them, dress shirts, colorful ties, acid washed jeans, and Nike hi-tops (Armisen and Samberg wear green sunglasses as well). Harris plays keyboard; Wilson, Elliott, and Michaela Watkins play violin; Moynihan plays tuba; Thompson plays harp; Hader plays saxophone; Hammond plays trumpet; Wiig plays electric guitar; Sudeikis plays double bass; Forte plays drum kit; Armisen plays synthesizer; and Samberg plays an Akai MPC 2000XL drum machine. At the end of the performance, Harris sheds a single tear.

In an early '80s-style instructional video, a nerdy man dressed like Carl Sagan (Samberg) shows viewers how to seduce women by playing chess, but the first two women (played by Nasim Pedrad and Abby Elliott) beat him. The instructor then changes the game to checkers and still gets beaten by a woman (Kristen Wiig). He tries Jenga, but ends up knocking the tower over. He tries eating glass, but ends up scaring the woman he's trying to seduce (played by special guest Olivia Wilde). The instructor (with his lips and mouth now bandaged up) gives up and lectures on how to hire a prostitute. The prostitute (played by episode host Jason Segel) offers sex to him for $5000, but the instructor only has $60. The instructor is stabbed and robbed of his money. Before dying, the prostitute comes back and beats him at chess.