- 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!
- Another road trip intro, this one coming from Walt Disney World.
- One time, Brad Garrett had to draw "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, 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).
- Dick Gautier spent all of sixty seconds 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 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 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 Ass of Yourself!"
- Off-screen, Bert Convy was a real prankster- according to a 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.