Whose Line is it Anyway?: 15 Absolutely Bonkers Moments

We can check on my head injury later, okay? I’m in the middle of a scene here!
Whose Line is it Anyway?: 15 Absolutely Bonkers Moments

Whose Line Is It Anyway? had some of the best improvisers on planet Earth.

We were happy just watching the regulars for hours and hours, but when they threw in guest stars like Robin Williams and Richard Simmonds (wait, what?), this show was bound to have some outrageous and memorable moments.

Colin’s meta green screen moment.

Colin green screen

Hat Trick Productions & Warner Bros.

“It’s horrible! Have you ever seen anything like it?!”

There was a great ongoing scene where Colin plays a newscaster in front of a green screen, but the screen’s contents are a mystery to him.

In season 2, episode 39, Whose Line producers put together a clip show of Colin (and Ryan) being utterly insane, and Colin being afraid of himself had everyone in tears.

Whose Tern Is It Anyway?

Colin & Ryan

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It’s just the last thing you’d expect Colin to say.

In this edition of “Greatest Hits” from season 5, episode 11, Ryan asks Colin what sound an Arctic Tern makes and his answer has Ryan (and everyone else) full-stop laugh for about a minute straight.

Wayne serenades a lunch lady.

Wayne Brady

Hat Trick Productions & Warner Bros.


This song rivals Adam Sandler’s “Lunch Lady Land”.

As a “singing strip-o-gram”, Wayne gets all kinds of spicy while (you guessed it) singing and stripping for this retired lunch lady.

Stephen Colbert shows off his skills.

Stephen Colbert

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There’s a slam poetry jam at the lodge tonight.

One of Whose Line’s many memorable guests was Stephen Colbert, who was a very skilled improviser at The Second City in Chicago.

His ski moves and off-beat but skilled rhymes about being in an avalanche are top notch.

Ryan breaks the desk, but doesn’t break character.

Ryan breaks the desk

Hat Trick Productions & Warner Bros.

It was season 3, episode 38, on a day just like today…

In “Party Quirks”, a host has to guess everyone’s secret characters, and in this round, Ryan’s character is "Carol Channing Whose Head Keeps Getting Stuck To Things”.

When Kathy Greenwood struggles to guess his identity, Ryan smashes his head into Drew's desk and shatters a neon light. Everyone checks for blood, but Ryan keeps the game going. A true professional.

Carol Brady smacks Jan.

I’ll give you a helping hand!

Florence Henderson’s first appearance was in a game of “Duet” with Wayne Brady and Brad Sherwood, where they serenade her in disco style, with very non-PG lyrics.

In this clip of “Helping Hands”, she aggressively berates Ryan Stiles' Jan Brady, smacks her and shoves meat loaf down her throat.

The worst (which made it the best) Irish drinking song.


In this now-infamous clip, the topic is “Yelling out the wrong name in bed” but after Drew Carey mumbled through his line, Ryan quickly picked up on this and responded by loudly mumbling gibberish on his turn.

No one keeps their composure, and what no one would describe as “good improv” actually gave us one of the most hilarious moments in the show’s history.


One from the revived show in 2013.

Olympians on Whose Line

Hat Trick Productions & Warner Bros.

What are you looking at, Wayne?

In season 1, episode 5 of the “new era”, Olympic synchronized swimmers Mary Killman and Mariya Koroleva joined in as the props for Colin and Ryan, who try so desperately to be funny while not coming across as creepy old men.

Robin Williams is the real Slim Shady.

Robin Williams

Hat Trick Productions & Warner Bros.

Clearly fresh off of his role in One Hour Photo.

The Whose Line gang kept up with one of the greats. Williams was his usual tornado of comedy, and it culminated with this epic game of Props. They just kept rifling off the goods.

Colin’s perfect double entendre.

This one somehow aired on network television.

In a round of “Scenes From a Hat”, the suggestion from the audience was ‘Things you can say to your dog, but not your girlfriend’.

There are tons of great lines in this one, but Colin just swung for the fences with his simple, yet brilliant, one-word answer… “come”.


Singing and spelling at the same time does seem hard at that pace.

Wayne was tasked with making up a song about Howard, an engineer picked from the audience. For some reason, Wayne was unable to correctly spell the name Howard. He kept putting in an extra ‘r’, spelling it ‘H-O-R-W-A-R-D.

On top of that, pianist, Laura Hall, inadvertently hit the tempo button and caused the song to go completely off the rails.

“We’re watching animal porn”.

Where did that come from, Colin?

A running gag in this particular “Greatest Hits” game was Ryan and Colin coming up with a bizarre TV Show that the fictional commercial was interrupting.

Out of nowhere, Colin began a joke about interrupting animal porn, before quickly realizing that he won’t be able to say that. The cast bursts out laughing, presuming that this part would be cut from the show, but it somehow made it to air.

A female bodybuilder gets handsy.

Female bodybuilder

Hat Trick Productions & Warner Bros.

For whatever reason, female bodybuilder Jane Tricker was a special guest for one of Wayne’s songs, and it got all touchy, feely as articles of clothing got removed.

But that caress…That caress really came out of nowhere.

The letter h (yes, a lower case h).

The letter h

Hat Trick Productions & Warner Bros.

In another great moment from “Scenes From A Hat”, the scenario was, ‘If lessons in love and sex were taught in the style of Sesame Street’.

There are some great ones before this ever-so memorable moment where Ryan bends over Colin to represent the letter ‘h’.

Richard Simmons.

Hat Trick Productions & Warner Bros.

You’d never suspect it, but Richard Simmons is somehow the best guest on the show.

He’s so quick and energetic (and constantly flirty) that the cast has to be on their toes to even keep up.

During the unforgettable game of ‘Living Scenery’, he was used as a telescope, and a ‘shiny’ deck chair (that was somehow wet) and sent the performers and audience into fits of uncontrollable laughter.

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