Howard's attitude is classic. There's always one person in a game of Trivia Pursuit that thinks they know the answer to every question they don't get.

The Moops…the answer is The Moops.

Robyn said 8, I could tell through the video. And Gary got the airport question correct

Gotta love classic Stern. One thing I loved about the show was that he always involved his crew.

This radio show shaved hours off my traffic commute into NYC to the point where I didn't want to get out of my car.

Howard is such a sore loser. I love it 😂

I love how Robin casually calls them dummies repeatedly.

"Call it in the air BOFF......."

One of the greatest segments during that era. I actually laughed audibly while watching this, even having listened to it on air originally. What's great is this show has had the ability to naturally allow itself to develop and transform, right from the beginning...

'They apologize to Howard' lol. Jackie had some good one liners.

is there ever a goddamn contest on this show that doesnt end in controversy?

Howard said he thought it was seven heard Robin start saying eight and cheaply took the point lol.

Lovey classic clip. BABABOOEY TO YOU ALL!!!

I LOVED listening to this show back in the 90’s! Thanks

0:45 call it in the air boff jajajaj

I grew up listening to Howard Stern. His voice was like a father to me.

These classic clips should be daily! Sooooo much content since 1994 when they got the E! cameras in there

An old clip straight from the source? ABOUT DAMN TIME BOYS. Thumbs up.

You guys are really hittin' em with the Hein, love the mix of new and older clips!

Howard cheated with the Apollo question, and Gary knew the airport question.

JACKIE WITH ALL THOSE DAM FINGER COTS ON LOL

Thank you so much for uploading. This is my favorite Stern era.

Love the old clips of the show! 👍🤘✊️

Oh my God. I can't believe Gary actually says boss that way. I thought that was Howard and Fred exaggerating. XD Lmao

Excellent segment. I smiled and laughed trough the entire clip...

You just know Gary could be ahead 30-0 & boff would still catch him

Golden era of Stern!!! xoxo The Clarences

Nice to see these

They wouldnt have even uploaded this, had howard lost lol

I remember listening to this live!

Robin is adorable. I love when they are just having fun, being themselves. Great clip.

gary is the brains behind the operation and u shit on him and make fun of him all the time, i love that dude

MORE of clips like these!

Gary won for several reasons: Gary got the airport question. Howard saw her lips. Howard made up the rules as he went along. For example: Once Gary reached 5 right, Howard said, give me a chance to tie it up. When Howard reached 6, What stopped Gary from saying give me a chance to tie it up? That logic could have went on forever.

Fun Clip. Thanks for Posting

Gary was robbed. Robin mouthed Apollo 8, because I instinctively said 8 to myself when she did it. It was a slight pronunciation but it was there. Howard showed how he is a sore loser with this clip.

Gary sounds like the narrator that plays the predators voice in To Catch a Predator 😅

7:24 I saww rit!

Howard names what he thought the first film with sound is.... Proceeds to name a silent film lmao

11:15 Howard's answer to the skyscraper question always cracks me up. Bayville! hahaha. The way he pronounces LA and SF are etched into my brain. XD

I knew howard would get superman's dog 😂

I can't believe neither of them knew who William Bonney was.

Classic video at 12 mins long ? It must be a cold day in hell! 10/10

Library of Congress should be common knowledge. Idlewild was also in Goodfellas.

Robin was looking good back in 96!!

Every SINGLE game! Howard lost and then bullied Gary into conceding defeat. Every goddamn time. And THAT’S why Gary ended up never believing he would beat Howard at anything anymore. Gary, the smartest and best-natured one of them. And therefore the one who always got portrayed as the idiot, only because he couldn’t compete with the narcissistic aggression and domineering behavior of those a-holes. Which is why I listened every day. I never got tired of hearing him get used as an emotional punching bag. So what the hell is wrong with ME?

Gary had to take a dive

Happy 58th. Flot Flot Gooey. You're the greatest

keep the old school uploads coming. foo foo boo high

Ahhh...these were the days!

It’s so crazy seeing these videos from just 20 years ago and seeing how much they have aged. Time is so scary.

And to think that todays show probably had 2 solid hours of Bobo and Marianne from Brooklyn

As usual, Robin is the impetus for the drama

Idlewild airport was in the movie Goodfellas.

"The Jazz Singer" was sound-on-disc, not sound-on-film.

wow 23 yrs ago!

10:33 oh the GREAT old days!

Oil and Vinegar

@6:18 😄😄😄😄 lmaooooo Jackie was the best

Robin and Howard ever have "a thing"? They, especially Robin, seem to look adoringly at each other.

the comeback

Good. Old. Days.

Robin loves Howard, look at her gazing at him

I think Gary missed some intentionally.

Apollo Ayyy-

good old days

Jimmy CARTER?! WHAT?! 🤣

"Apollo eigh..." 😂

How's Philadelphia not an old city? Lmaooooo

Gary looks like a king

I can't believe this is from 1996.

Gary is a good dude with big choppers 😁

Awww my birthday!

Hank was such a good guy.

Gary won

“call it in the air bawf”

Chicago!

Robin was a cutey

I didn't know any questions

i cant tell if howard is looking older or younger as time goes on

Dell'Abate-- Mr. 5"

Who is William H Bonney? Howard didn't know, and neither did BabaBooey. This is just inconceivable to me.

Robin and her Adderall bumps

Robin is such a beautiful spirit.

06:18 LOOOOOOOOL Jackie hahaa...

Gary should have put up more of a stink over Idlewild.

Fa Fa Foamy should've won that...I think Howard DID see Robin begin to say "Eight".

Lol I love the fact that Superman is part of American Literature, and I'm not being sarcastic

those chompers are monolithic

Howard was different back then. He would never agree to this now.

I bet Gary can eat chicken wings in one bite.

Hahahahahahaha this is still unbelievable

by boff, I nebber win boff.

Only 1 city other than NYC could've had skyscrapers back then. They should've always have gotten different questions.

Noine!! Hey now!!

I miss the days when they would play games on the show. I loved the homeless game and the stripper game.

Ah, K-ROCK, good memories.

It’s parimutuel betting bawf

Saul Goodman's first gig

Film film with sound is Don Juan, not the Jazz Singer...