Dating Confessions by You "I love how nice, sweet, pretty and caring you are. I hate how I'm bored to tears. Mom would be proud, but my libido is AWOL. . . "
Much is made, even elsewhere on this list, of Letterman or Conan's ability to entertainingly defuse and interact with a guest gone haywire. While their reputations are certainly deserved, let's give a little credit to Dick Cavett, who had to deal with Sly Stone. Notable: as if inspired by this appearance, President Nixon would pass the Controlled Substances Act just three months later, criminalizing cocaine and (at least theoretically) causing flamboyant celebrity appearances such as this to disappear like so much white, powdery dust in the wind. — J.B.
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14. Jean-Claude Van Damme on Brazil's Domingo Legal, 2007
In 1998, the R&B group Next came out with the hit single "Too Close," a little ditty about a man who gets a hard-on while dancing. Jean-Claude Van Damme later had the misfortune of living out this song on television. (At least it in happened in Brazil.) Okay, so it's not exactly an interview, but it's certainly unique. — L.A.
13. Iggy Pop on The Late Late Show with Tom Snyder, 1980
By 1980, Iggy Pop was a shadow of his former self. No longer the wiry, energetic Stooges frontman — nor even the drug-addled Bowie acolyte — Pop had become a jittery, gap-toothed junkie, seeking a home in the smoking ruins of punk rock. This interview with the always-unassuming Tom Snyder is a painful seven-minute fumble for coherence. It isn't uncommon to see a celebrity go supernova, but it's plain unsettling to witness one long after the implosion. — John Constantine
12. Tracy Morgan on Late Show with David Letterman, 2008
Let's set aside speculation about whether the 30 Rock star was high or only pretending on this January 2008 Late Show cameo, and give the man some credit: he knows how to give a memorable interview. Whether making cryptic remarks about Dr. Phil's legal name or yelling non-sequiturs ("I'm crazier than a box of rocks!"), Morgan brings a ne'er-do-well raffishness you just don't see enough on late-night TV. Maybe he's battling some inner demons, but — if his comments about his "DUI gremlins" are any indication — talk shows seem to be his way of exorcising them. — C.L.
11. Courtney Love and Madonna post-MTV Video Music Awards, 1995
Madonna was in her early-Evita phase when Courtney Love crashed this post-VMA interview between her Madgesty and Kurt Loder. When Love throws a compact at Madonna's head, Loder invites her to join the interview, despite Madonna's objections, and what follows is a barrage of Courtney's crazy stream-of-consciousness. A decade before Joaquin Phoenix, Love says she'll change careers because "this whole rock-star thing is not working out," quotes Warren Beatty from Madonna's doc Truth or Dare, and finally forces Madonna and her publicist to flee. Madonna summed it up best when she said, "Courtney Love is in dire need of attention right now." You know you're in trouble if you're hearing that from Madonna. — J.C.
