Graduated from Middlebury College in Vermont, where he often faxed jokes to Norm MacDonald to use on Saturday Night Live (1975)'s "Weekly World Update".
Hired as a staff writer at Late Show with David Letterman (1993), when he was 21 years old. At 24, he was promoted to head writer, making him the youngest head writer in the program's history.
[on the bestseller 'Tuesdays with Morrie']: I realized the guy who wrote that book only spent one day a week with Morrie. If he'd spent more time with Morrie he'd realize that by Wednesday Morrie would've run out of things to say, and by Friday you'd want to strangle the guy.