CONANDRUM
Interviews
Conan O'Brien, a "Simpsons" writer with little TV experience, debuts as Letterman's "Late Night" successor tonight. Backed by producer Lorne Michaels, O'Brien hopes authenticity will win audiences despite pressure and skepticism about his relative unknown status.
17-year-old Brookline High senior Conan O'Brien won a national writing award for "To Bury The Living." He excels academically, edits the school paper, admires Hemingway and E.B. White, and remains undecided about college.
Conan O'Brien discusses his podcast empire, new Max travel show "Conan O'Brien Must Go," reflections on late night's decline, the 2010 Tonight Show controversy, Lorne Michaels, and becoming an empty nester at 60.
1993's crowded late-night TV landscape features Jay Leno, David Letterman, and newcomers Chevy Chase and Conan O'Brien competing for viewers. O'Brien, 30, brings likable humor from his Simpsons writing background. Chase returns with SNL-style comedy. Leno focuses on consistency. All face high stakes as NBC, CBS, and Fox battle for late-night dominance.
1999 phone interview with Conan O'Brien covering his daily routine, desk items, fame's minimal impact on his life, influences like Letterman, working with Andy Richter and Robert Smigel, favorite sketches, guitar hobby, and hopes for touring the show internationally someday.