- Baby Blues pointed out that the game's Luck-Based Mission characteristics make it as hard to deliberately lose (i.e., to let a small child win) as it is to aspire to win yourself.
- A Get Fuzzy comic had Satchel using a "Candyland'' board in conjunction with a Ouija widget; and wondering why a ghost would pass through multiple dimensions to tell him "Gumdrop, Gumdrop, Lolly" when Bucky tells him he needs a Ouija board to make the widget work properly.
Live-Action TV
- Cory from Boy Meets World laments in one episode that he spent his Saturday night playing Candy Land with his sister, "and lost", as if losing a game of pure chance is more pathetic than winning it.
- Shown in the Mystery Science Theater 3000 episode Parts: The Clonus Horror.
- Nurse Jackie has the main character playing the game with little girls and a boy in "Heading North".
- That '70s Show has Eric Forman stashing away money in a Candy Land box. It is later revealed that the gang hides a different kind of stash in the same box.
- X-Play reviewed the 2000 version of the game once...during a game drought.
Music
- Katy Perry's music video "California Gurls" was heavily based with this. Only Hotter and Sexier.
Toys
- Wacky Packages has parodied the Candy Land board game a couple of times: as "Brandy Land" in Series 12 and as "Cranky Land" in the January Monthly Series.
- The webcomic Dan and Mab's Furry Adventures has Candy-Land Adventures appear in #1453
and #1460. It transforms this game into an RPG like Dungeons & Dragons, complete with rolling dice, fighting monsters, and arguing about the rules. Roles include Peppermint Paladin and Rogue of Red Hots.
- It is a Running Gag in Board James that Bad Luck Bootsy wants to play Candy Land (instead of whatever game the episode is about). He briefly gets his wish in the Season 3 finale, currently the series finale... in rather dark and bloody circumstances.
- Animaniacs: In "Meatballs or Consequences" (a parody of The Seventh Seal), Death challenges the Warner siblings to a game of chess, but they don't know how to play, so he settles for checkers instead. Dot eagerly asks if he has Uncle Wiggily or Candy Land, but being The Grim Reaper, he doesn't.
- The Simpsons: In "Any Given Sundance", one scene has Marge going into Sundance festival theaters that are showing indie dramas with innocent-sounding titles. One of those movies is Candyland, which she thinks it's based on the game, but it turns out to be about drug addicts.
- VeggieTales: In "Larry-Boy and the Fib From Outer Space", Larry and Alfred (Archibald) play this game. Larry is stuck in the Molasses Swamp for at least 38 turns as Alfred is able to immediately advance all the way to Princess Lolly. Amusingly, this almost certainly means Larry was originally ahead of Alfred.
