In 2004, my wife and I started watching Last Comic Standing. We had missed the first season entirely, but the second season won us over in just a few episodes. Though John Heffron ultimately won the title, we were blown away by Alonzo Bodden (who won season three), Jay London (whose strange appearance and odd presentation made us laugh hysterically — "I'm the fourth guy from the left on the evolutionary chart."), and Kathleen Madigan — a little spitfire who used observational humor to disarm her audience every time. She didn't do as well on season three, but came back as a talent scout in a later season.
We are also huge fans of Lewis Black, who is one of Kathleen's friends and ardent supporters. Anywhere we've seen Lewis, we've also seen her, including on Lewis Black's Root of All Evil. And, although we saw Madigan's last comedy special In Other Words a few years ago, we really hadn't seen her with a new stand-up routine for a while.
Consequently, when we saw that she had a new stand-up comedy special, Kathleen Madigan: Gone Madigan, I knew we'd have to catch it on DVD without all the bleeps... We weren't disappointed. She's in rare form with bits about politics, American culture, and her own family. It's that kind of self-deprecating humor that keeps me coming back.
Madigan starts the routine by making fun of her own hypochondria. The web (specifically WebMD) has probably done more to advance hypochondriacs than actually help sick people. She made a New Year's resolution to swear off her own streak of "self-diagnosis" after spending the prior year diagnosing imaginary illnesses. As she says, "I had ankle cancer for a while... Then I had shrinking eyeballs... That was weird..."
As she talks about her USO trip to entertain the troops in Afghanistan, she suggests that after hearing of some of the successes there--building roads, schools, and police stations--that maybe it's time to invade Detroit. They could use the boost!
It's her seamless transitions, from personal stories to commenting on something more substantial like the economy of Detroit, that really makes her routines flow. Where some comedians build in pauses for transitions, she just keeps things rolling from one bit to the next.