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15. Sly Stone on The Dick Cavett Show, 1970



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.
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.




                 


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32 Comments

Too bad you didn't have room for one of my favorite Tom Snyder regulars - "Joey" the hit man.

rh commented on 02/26

how is it possible that i have never seen this tracy morgan clip before? how have i lived?!!

mee commented on 02/26

You missed the hilarious Oliver Reed interview on 'Aspel'...

KT commented on 02/26

You totally forgot Steve-O on the Too Late with Adam Carolla Show https://www.youtube.com/watch?v=_rafFvbCf4Y

poo commented on 02/26

You have #19 mislabeled. That was not "The Late Show with David Letterman." This clip is from 1986. Letterman did not move to "The Late Show" on CBS until 1993. The clip you showed is from "Late Night with David Letterman" on NBC (later "Late Night with Conan O'Brien," and now "Late Night with Jimmy Fallon").

JS commented on 02/26

The same goes for #5 and #1.

JS commented on 02/26

Thanks! Titles have been fixed. - Ed.

Ed commented on 02/27

I really don't think that the Iggy interview is as shocking or painful as you're making out. A gap-toothed junkie he might have been at the time, but this interview is pretty much par for the course for an Iggy interview from the 70s and 80s. I thought he was as eloquent and witty as ever, if obviously 'addled', and Snyder was taking it with good humour. For a real Snyder interviewee meltdown, his interview with Lydon and Wobble from PiL takes a bit of beating. https://www.youtube.com/watch?v=_BZ2UoBZzEI

DM commented on 02/28

My mistake, I meant of course Lydon and LEVENE.

DM commented on 02/28

How could you leave out Joe Namath's drunken interview with Suzy Kolber? "I want to kiss you"! Classic! What an oversight!

DSE commented on 03/06

Re: Whitney Houston Interview -- this is not Barbara Walters doing the interview, it's Diane Sawyer.

CC commented on 06/04

Don't see what is funny about these. Painful to watch, cringe-worthy is not fun! Best forgotten.

MMM commented on 09/25

These are great. Cringe-worthy perhaps, but fascinating and a great lens on our often strange modern culture.

got commented on 09/25

Tracy Morgan should just be on everything, all the time. Loved him nodding like a crazy man at Taylor Swift during the VMAs. He's insane and awesome!

lala commented on 09/25

What about Artie Lange on "Joe Buck Live?" He hijacked a boring talk show and turned into a hilariously filthy piece of Borscht Belt performance art.

BF commented on 09/25

In many instances -particularly with Letterman - the odd behavior is obviously staged with the host feigning surprise. Let's not be naive here.

wp commented on 09/25

DSE.. I agree with you there!! That Namath interview was awwkkward!

RS commented on 09/26

I love the Sam Phillips interview.

Bell commented on 09/26

The Iggy interview was great. I think the Nietzsche reference (Apollonian and Dionysian) went over John Constantine's head. Constantine is the one fumbling for coherence.

bhny commented on 09/26

John Constantine, did you really listen to the Iggy Pop interview, because he was very coherent, smart, witty, earnest, and self revealing throughout. Tom Snyder seemed interested in everything he had to say. Wasn't a trainwreck at all!

jz commented on 09/26

What about Mary Lou Henner on The Tonight Show. That was screamingly funny and incredibly painful at the same time.

DW commented on 09/28

What about Grace Jones and her 8-ball on Letterman in 1986?

cb commented on 09/28

I'm sad Beck's first interview on 120 minutes wasn't there. The one where he doesn't say anything, but just tosses his boot at the set. That was amazing.

LL commented on 09/28

How about Carson with Zsa-zsa and her cat? I'd've thought it was a total setup, but she stormed off and didn't come back. Short, but classic!

ts commented on 09/28

Go look up "Molly meldrums interview with Iggy pop" on australias "countdown" music show from the 80s. Its completely hilarious. Iggy was so fucking high.

dmx commented on 09/28

I gotta call "too soon" on Farrah.

mjk commented on 09/29

a drunk Mitch Ryder interviewed by a German before a gig, this is on a Rockpalast dvd. Henry Rollins, when with Black Flag inverviewed by a punk kid. Can be found on youtube

ssk commented on 10/04

I agree with the Artie Lange interview on Joe Buck's boring show. Certainly strange to Buck, but HILARIOUS to me.

m2 commented on 10/06

No, Michael Jackson?!

SM commented on 11/07

Howard Stern's appearances on Arsenio or Snyder or Leno? C'mon!

KB commented on 11/28

Oliver Reed's interview on Aspel OR Letterman would have fit somewhere.

zcs commented on 12/10

Damn, part 1 of the norm mcdonald/conan interview is a little rough, but they both get funnier, and more irreverent as it goes along. part 3 is pretty brilliant actually.

KCG commented on 12/14
 

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