I use to be a big Letterman fan back in the day, but haven't watch him in a long time.
This are some of the most painful interviews ever caught on tape.

Joaquin Phoenix drugged out
http://www.time.com/time/specials/packages...1879160,00.html

Farrah Fawcett goes off the deep end
http://www.time.com/time/specials/packages...1879221,00.html

Drew Barrymore flashing Dave
http://www.time.com/time/specials/packages...1879143,00.html

Kristen Stewart, if she only had a brain.
http://www.time.com/time/specials/packages...1879162,00.html

Madonna proving she's got bigger balls then most guys <<--- my fav
http://www.time.com/time/specials/packages...1879214,00.html

Paris Hilton's post slammer interview
http://www.time.com/time/specials/packages...1879238,00.html

Andy Kaufman proving why he only wrestled girls
http://www.time.com/time/specials/packages...1879236,00.html

Crispin Glover ( aka Marty McFly's father) goes mental
http://www.time.com/time/specials/packages...1879235,00.html

Michael Richards tres to save his career after the N word blowup, but only makes it worse.
http://www.time.com/time/specials/packages...1879308,00.html

Harvey Pekar attacks GE forcing Dave to defend them because they sign his check
http://www.time.com/time/specials/packages...1879315,00.html
This one sucks except seeing how defense Dave gets

lol to Crispen Glover - no wonder he disappeared .

Jaquin Pheonix- is it possible to be as hammered as he is in public?