6. Letterman Gets Married (March 23, 2009)
Dave's never getting hitched again: That was the impression shared by most Letterman observers. After all, he'd been married once in his twenties, and he and his longtime girlfriend Regina Lasko seemed content not tying the knot. But on March 19, 2009 — after 23 years as a couple (and a five-year-old son, Harry) — the two married at a Montana courthouse. A few days later, Dave announced the news on the Late Show, looking pretty pleased but also a little terrified. Letterman told the audience, "People say, 'Geez, Dave, you were together so long — does it feel any different?'" Dave then paused, dramatically, for comedic effect. "And I say, 'Yeah.'" Long pause. "It does."