Top 10 Funniest Whose Line Is It Anyway Moments

Whilst Wayne Brady tends to handle the song styles, improv world staple Colin Mochrie will usually handle the press conferences. This is a game in which a performer has to answer questions from the other three cast members, in character, without knowing who they’re playing. Only when they’ve deduced what their character is and what they are doing does the game end. One Press Conference saw Colin playing Batman, delivering the news that he was coming out of the closet. As well as the hilarious reporter monikers and their respective press labels, the clues were brilliantly worded. As always, Colin stayed in character right to the end.

If we continue to use Drew Carey’s uncontrollable laughter as a measurement for how funny a “Whose Line” moment is, then clearly this entry has earned its place. Carey wasn’t even hosting when this Three-Headed Broadway Star game went completely off the rails. They were supposed to sing a song about a given topic one word at a time, but Ryan Stiles, Wayne Brady and Drew Carey are almost completely incapable of navigating this nightmare. Singing multiple words at once, breaking up words into syllables and then just losing the plot altogether are part of what goes wrong here. It got so bad that Drew couldn't even end the segment, leaving Ryan to take over.

He may have all-but-disappeared from the public eye, but the eccentric and flamboyant fitness personality has cemented his status as a “Whose Line” legend–with only one episode. Simmons, who seemingly has an endless supply of energy coursing through his veins, was in fine form as he made his way out to an ecstatic live crowd for Song Styles. However, a grateful Simmons returned later that episode for a… well, shall we say suggestive game of Living Scenery, wherein he played all the props… including a telescope. Again, as Carey’s inability to keep-it-together demonstrates, it was Simmon’s Jet Ski that sent the moment into hysterics.

We’ve already established that Wayne Brady is the musical heart of the show. The opposite end of that spectrum really is poor Colin Mochrie who… well, just isn’t a musical guy. He is an extremely funny one, however. In fact, when Colin simply accepts his shortcomings, including his well-documented inability to rap with any sort of discernible rhythm, he manages to make comedy gold. Inadvertently becoming a running theme, Colin’s lack of hip hop prowess has been pointed out by the man himself, as well as his forgiving co-stars.

While Colin can give a great press conference and Wayne has the voice of a vengeful angel, Ryan Stiles brings his own unique skill to the table with a particular impersonation. Ryan's party trick is that he has a dead on Carol Channing voice, and it has been used to maximum effect thanks to suggestions from the audience. The “Hello Dolly” actress has appeared more times in “Whose Line” than she did in movies. Ryan’s impersonation is so good that other guests will often do an impression of Ryan's impersonation, instead of a direct facsimile of the original Hollywood Starlet.

Though the show had been in existence in some form for nearly two decades by this point in time, many of us were introduced to “Whose Line is it Anyway” during season three, as the legendary Robin Williams entered the playing area. Despite filming “One Hour Photo” at the time (his hair is bleached blonde), the actor managed to join in for an episode that no one could ever forget. Partaking in Scenes from a Hat, Hollywood Director, and more, Williams looked truly at home. Truthfully, we could probably devote a separate list of moments from this particular appearance, simply take our advice and watch the whole thing from start to end and be reminded of just how one-of-a-kind Robin Williams really was.

During a game of Party Quirks, each improviser is given an envelope describing who they are to play, and it is up to the guest to determine who they are. But one particular party took a surprising turn. Ryan, playing "Carol Channing whose head keeps getting stuck to things" careened crown-first into the neon light on the face of Drew’s desk, and shattered the glass tube. Yet Ryan (who isn’t sure if he is bleeding from his scalp) doesn't break character for a moment. In fact, he turns the whole thing around. Even as the other cast members stop playing to check on him, he continues to make it funny–causing Carey to fall out of his chair laughing.

Over the years, the cast of the show have made no secret of their disdain for the often censored Irish Drinking Song, a round whereby every performer has to sing one line of a song and rhyme the second and fourth. For a song based on calling out the wrong name in bed (itself carrying the potential to be censored), Drew threw a garbled second line for Ryan to rhyme with. Which he did, with gibberish. The song completely fell apart, the performers corpsed with the exception of Colin, carrying the whole number with one word: “Meow.”

Colin Mochrie and Ryan Stiles were regularly invited to the original British show, and their rapport and real-life camaraderie continued on the US version. Yet, despite their ability to perform together with a near-telepathic understanding, it’s the moments when they’re not on the same page that elicit the most laughter. During a game of Greatest Hits, Ryan posed a riddle, expecting Colin to answer “owl”. This would be a segue to the band “The Who”. But Colin’s answer was … unexpected … This threw Ryan off completely, causing him to laugh uncontrollably for the whole segment. Poor Ryan never recovered…