- September 21, 1972: A contestant spun the category "Annual Events", whose slide used art of a groundhog. When the question turned out to be about Groundhog Day, the contestant pointed out that the answer was on the slide. Jack Barry was quick to deny that it was a groundhog, and the contestant remarked that the animal looked more like an otter. The other contestant then spun and came up with a triple (two Annual Events and a Joker), to which he said "I believe I'll take that otter for $200."
- Early 1973: In one game, the slots seemed to favor Horse Racing and Bing Crosby over the three other categories. When Jack asked for the title of Crosby's autobiography, it turned out to be an Unexpectedly Obscure Answer.
- Early 1973: In a game with a category of British Singers, Jack noted that the picture of the singer of the slide reminded him of "Tom Jones on a bad night". Then he couldn't ask the question he had in his hand because the answer was Tom Jones!
- October 1978: During big winner Hal Scheer's first appearance, one of the categories in his second game was The Olympics, with Hal getting a question at one point about how many interlocking rings are in the Olympic logo. The problem? The category's slide used the Olympic rings as part of its graphic, essentially giving away the answer! Although the discrepancy wasn't caught until after the game had been completed, Jack explained what happened at the end of the show, and while Hal claimed he wasn't looking at the category slide when he answered the question correctly, Jack stated that in the interest of fair play, the challenger that Hal defeated would be invited back to play again on a later episode.
- Once, Jack was set to reveal the game's categories, but they just wouldn't come up on the screen, causing Jack to vamp for about 30 seconds or so. When the categories finally came up, they were the wrong ones.
- 1980-81 season: An over-eager contestant in the Bonus Round pulled the lever so hard that she broke it off. Jack replied, in pretend anger, that "You broke our wheel!"
- Taped December 1977: A few years earlier, a champion contestant pulled the lever so hard that he caused the entire handle to be dislodged from its base. Luckily for him, it was the winning spin (he had $975, and he spun $50-$100-$50) and Jack jokingly said that it would cost $1,200 to fix it.
- An employee of KCOP-13 (where the show taped in the early-to-mid 80s) recounted "During one taping, a contestant became a little too exuberant during the bonus round (when they pulled the large slot machine handle to the right of the machine) and wound up snapping off the plexiglass column at its base. All of the light bulbs inside the handle cascaded to the floor in a heap, still fully lit. Jack became completely flustered, and the whole scene was quite hilarious. Unfortunately, I doubt you'll ever see it on a blooper reel as Dan Enright immediately took control of the tape room and ensured no one made any unauthorized copies."
- Late 1979: From Joker! Joker! Joker!...Jack: What about your daddy, what does he do?
Contestant: He sells cookies.
Jack: Cookies? To whom?
Contestant: To the movie theaters...
Jack: Anybody else?
Contestant: ... and fat people.
Jack: Fat people.
- 1985(?): During the Cullen era, one game had Sex Symbols as a category, but as a gag, the staff replaced the animated blonde normally featured in said category's graphic with an actual photo of Bill during the 50s, which broke him up when he first saw it while reading off the categories at the start of the game, then again when it first came up on the wheels!
- This 1990 episode has Pat Finn and the winning contestant tap-dancing to the theme.
- 2018: One episode had Biz Markie involved in the category "You Got A Disease", entailing him playing a piano, wearing a weird wig and singing silly songs to hint towards the right disease.
Funny / The Joker's Wild