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When we first posted this list in February, it was in response to the instantly iconic Letterman interview with a bearded, bespectacled, near-catatonic Joaquin Phoenix. At the time, we were pretty sure we'd seen the ne plus ultra of celebrity madness, but this week's Mackenzie Phillips shocker on Oprah probably retakes the cake. But then, there's a lot of cake to go around, as this compendium of bizarro TV moments should reassure you. — Peter Smith
20. Gary Busey and Jennifer Garner on the Oscar Red Carpet, 2008



Gary Busey is no stranger to weird public antics (remember: he will tear out your endocrine system!), but this red-carpet appearance at the 2008 Oscars is the jewel in his madman's crown. When Busey interrupts Ryan Seacrest's interview with Laura Linney and Jennifer Garner — and plants a wet one on the petrified Garner's vulnerable neck — the ladies do what pretty girls in bars have been done for decades: smile sweetly at the crazy man and back away for some "girl talk." Busey's later apology was almost as incomprehensible as his original transgression. — Lindsay Armstrong

19. Sam Phillips on Late Night with David Letterman, 1986




In 1986, Sam Phillips — the founder of Sun Records and producer for such rock legends as Elvis Presley, Johnny Cash and Roy Orbison — forged his own legend when he showed up on Letterman high as a kite. Phillips had just been inducted into the Rock and Roll Hall of Fame; it's logical that he wanted to celebrate, but everything that transpired next completely defied logic. Here, Phillips set the template for the Joaquin Phoenix interview — looking and behaving like a Montana militiaman is the surest way to Dave's heart. — Cyriaque Lamar

18. Mike Tyson on WWOR-TV/UPN 9 News (Secaucus, NJ), 1999



Nobody expected Mike Tyson to be Proust in this live interview, but then again nobody — least of all New York sportscaster Russ Salzberg — expected sixty-four seconds of expletives, threats, and a terrifyingly awesome demand to "turn off your station." In this clip from January 1999, Salzberg attempts to speak with Tyson about his comeback match with Francois Botha. After his famously ill-fated fight with Evander Holyfield, Kid Dynamite apparently had a chip on his shoulder (or some earlobe between his molars). — C.L.

17. Richard Simmons on Late Show with David Letterman, 2006



"I'm getting dizzy." This confession should be unusual at the beginning of an interview, but it is, after all, Richard Simmons. The man's history with David Letterman is a storied one, so it's hard to pick just one Late Night appearance for this list. The episode where Letterman doused Simmons with a fire extinguisher might seem like the frontrunner, but Richard's insistence that his vegetable steamer has a brain puts this one over the top. While Dick and Dave quibble over the price of the thing, it goes off like a bomb, and sends Simmons screaming across the room, patting his hair to make sure it's still on his head. Immortal. — Marian Lorraine

16. Norm MacDonald on Late Night with Conan O'Brien, 1997



Norm MacDonald was on top of the world — or at least the Weekend Update anchor desk — when he visited Conan in 1997. Though Conan prefaces the interview by saying Norm's been quite ill, we're not sure his incoherent ramblings can be blamed solely on bacteria. MacDonald reveals his scintillating creative mind, his slurred, incoherent rambling showing exactly why SNL in the '90s just got, um, better and better. He repeatedly references "ass fluids" and insults the disabled (combining both when discussing Larry Flynt!), then attempts to spread his love/germs on fellow guest Courtney Thorne-Smith. Conan sums up the interview by calling Norm "the biggest ass I've ever met." — L.A.



              


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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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