Recurring Guest Characters Jon Stewart 6 guest appearances Michael Stipe 4 guest appearances Buddy Cole 4 guest appearances Charlie Rose 3 guest appearances Matt Damon 3 guest appearances Grandmaster Flash 3 guest appearances Bill Clinton 2 guest appearances Bryan Cranston 2 guest appearances Henry Kissinger 2 guest appearances Jeff Tweedy 2 guest appearances Joe Quesada 2 guest appearances Katie Couric 2 guest appearances Mandy Patinkin 2 guest appearances Neil deGrasse Tyson 2 guest appearances Toby Keith 2 guest appearances Vince Gilligan 2 guest appearances Willie Nelson 2 guest appearances Terry Gross 2 guest appearances P.K. Winsome 2 guest appearances Dr. Del Vecchio 1 guest appearances ⇤ « 1 2 3 4 5 6 7 » ⇥