* [[https://www.youtube.com/watch?v=SFTBpNtxVJA One particular intro]] of WLOD emanating from Central Park in New York City.
-->'''Bob Hilton''' (after the horse in Bert's hansom cab refuses to move): Kick the horse!
* [[https://www.youtube.com/watch?v=7l6sc6U9hyA Another road trip intro]], this one coming from [[Ride/DisneyThemeParks Walt Disney World]].
* One time, Creator/BradGarrett had to draw '''[[UsefulNotes/AbrahamLincoln "FOUR SCORE AND SEVEN YEARS AGO OUR FATHERS BROUGHT FORTH ON THIS CONTINENT A NEW NATION, DEDICATED TO THE PROPOSITION THAT ALL MEN ARE CREATED EQUAL."]]''' For the record, yes, [[NotMakingThisUpDisclaimer that's exactly how it was written on the card]], and yes, the guys managed to solve it (although they only needed to get part of the phrase to get credit).
* Creator/DickGautier spent all of sixty seconds [[https://www.youtube.com/watch?v=7-evqbRwSEc?t=205 failing to get the guys to guess "THE PURPLE PEOPLE EATER"]]. What ''really'' made this moment was the fact that, despite there being markers for [[ColorCodedForYourConvenience red, blue, and various other colors]], there was ''no marker for purple'', leading to Dick desperately mixing various colors trying to communicate "purple" to his teammates.
* From the daytime version, Vicki [[https://www.youtube.com/watch?v=QIwG1zl3uc8#t=14m46s accidentally reveals the answer to a puzzle before the other team had an opportunity to guess.]]
-->'''Vicki Lawrence''': "This is ''Win, Lose, or Make an [[SoundEffectBleep Ass]] of Yourself!''"
* Off-screen, Bert Convy was a real prankster- according to a [[http://www.illustriousgameshowpage.com/gene1.html phone interview with announcer Gene Wood]], at one point during this show's run, he got the UCLA marching band to play outside Burt Reynolds' house at 6AM!
* From the 2014 Disney Channel revival: In his second episode, Garrett's reactions to how crazy insane some of these drawing challenges can be.