Before the events of Toy Story 3, Chuckles was owned by Daisy, living at her house, and it seemed he wore a constant smile. He was also a witness to see Lots-o'-Huggin' Bear, or Lotso for short, being unwrapped by Daisy during Christmas. The fact that his old friend Lotso was Daisy's favorite failed to slip past Chuckles' eyes because Chuckles claimed that he never saw a toy being more loved by any other kid. He was also a very good friend to Big Baby and Lotso during the time of being under Daisy's ownership.
Sadly, one day would ultimately put this friendship to an end: one day, while playing with Lotso during a picnic, Daisy had went to eat lunch and accidentally left Lotso, Chuckles, and Big Baby on the ground. After lunch, because she had a fun-filled day and a good lunch, Daisy fell asleep. Because of this, Chuckles, Lotso, and Big Baby were accidentally (purposely as Lotso would put it) left behind. Lotso believed that his old owner Daisy would return for them one day, and they waited for quite some time for her return. After waiting for a long time, and one rainy day, the trio finally gave up waiting until she came, so they went to her if she wouldn't go to get them. When they finally got to her house, it was too late because Daisy had claimed another Lotso bear to compensate for the original Lotso that she had accidentally abandoned. Lotso was heartbroken as a result. Then Lotso, filled with sorrow, had snapped: the jealousy, bitterness and resentful side of him shown, he then decided to leave his former friend. Chuckles had tried to confront Lotso, knowing that his actions were out of anger, and even pointed out to Lotso that Daisy had only replaced him and that she still loved them all. However, this didn't bend Lotso's will at all. Instead he shouted back at Chuckles that she replaced all of them, not just Lotso himself. Chuckles then saw Big Baby's pendant being torn off by Lotso and being dragged away, shouting at Big Baby that Daisy had no love for him anymore. Chuckles then grabbed the pendant and stuffed it in his pocket, the only thing that would have caused Big Baby to see the light because Big Baby still had love for Daisy, that had the inscription "My Heart Belongs To: Daisy" and tagged along with Lotso and Big Baby, begrudgingly.
The three lost, cast-off, unloved, unwanted toys then hitched a ride on a Pizza Planet truck until they fell off due to the truck hitting a bump, and they wounded up at the Sunnyside Daycare, where Lotso transformed it into a prison (with Big Baby working as his lackey), much to Chuckles' dismay. Eventually, Chuckles was damaged (most likely by Lotso) and that was when Bonnie found him and took him home with her (he also implied that many toys that were damaged like him weren't as lucky as he was).
Toy Story 3
Chuckles makes his debut while Woody is at Bonnie's house. When Woody mentions Sunnyside, Bonnie's other toys become surprised to see that he has made his escape without incident and asks him how he did it. Woody asks them what they meant, to which Mr. Pricklepants describes Sunnyside as a toy prison where an evil, strawberry-scented bear is at power. Woody asks his new friend why, and Mr. Pricklepants directs him to Chuckles, who tells Woody the story of Lotso's past and hands him the pendant that once belonged to Big Baby.
During the end credits, Woody shows him a drawing of the latter smiling made by Bonnie. This caused Chuckles himself to smile, presumably for the first time in years. He is also shown smiling (possibly amused) as he and the other toys gather around to enjoy Buzz Lightyear and Jessie perform a paso doble to the Spanish version of the song "You've Got a Friend in Me" in front of them.
Toy Story Toons
In Hawaiian Vacation, Chuckles is seen when Woody announces to the toys that Bonnie has left on vacation for her winter break vacation. A little later, He is seen playing poker with Buttercup, Hamm and Mr. Potato Head (who got interrupted by his his wife). At the end, he is playing a peaceful song on a lunchbox to Barbie and Ken (who are having dinner) with a guitar, but performs a faster song with the Aliens and Monkeys when Buzz starts performing a fire dance while in Spanish Mode.
When his former owner, Daisy, had owned him, Chuckles was once happy. Ever since Lotso became evil and took over Sunnyside, he became down, brokenhearted and depressed (though he still smiles in toy mode when humans are around). At the end of Toy Story 3, when he sees the picture that Bonnie (his current owner) drew for him, the clown smiles on his own for the very first time in years.
Chuckles is a toy clown with blue wilted hair that used to be straightened up when his previous owner, Daisy, had him. He also wears a bright yellow shirt with dark yellow spots, a clown collar, cuffs on his sleeves, purple suspenders, with red gloves and shoes made of rubber.
- It could be inferred that Chuckles' left button got broken as it appears to be missing a thread and is slightly cracked.
- Chuckles originally (as shown in flashbacks in the movie) smiled all the time, and his hair was up. But after his time in Sunnyside, Chuckles became depressed and only frowned with his hair down (the lowered hair possibly being a result of wandering in the rain during his flashback).
- In a part of the flashback scene about Lotso in Toy Story 3, his voice sounded somewhat different, implying that it likely changed over time. However, it is unknown as to why Chuckles had a silly, high-pitched, clownish voice (performed by an uncredited Bob Peterson) when he is mostly heard speaking using Bud Luckey's primary gruff, reserved, elderly-sounding voice. It could be that his voice sounds more silly when he's happy, and more gruff when he's sad.
- In Toy Story 3, even though he never smiled around Woody and Bonnie's toys after his horrible time at Sunnyside, when he goes into his toy mode, Chuckles actually smiles when the humans are present. Though if one looks closely in the scene where the toys meets Bonnie's toys, Chuckles can be seen smiling when he is greeted by Mrs. Potato Head.
- It seemed likely that Chuckles (due to his attachment with Daisy) refused to be a lackey of Lotso's during the latter's self-proclaimed rule in the movie.
- When Chuckles got broken (as evidenced by his sad story), even though this is never said in the film, it may be possible that the culprit wasn't one of the kids at Sunnyside. Lotso may have been the one that broke Chuckles (like how he broke Chatter Telephone for helping Woody escape). When he lifts his right armpit while explaining he was broken, you can see stitching on the right side of his body.
- Although Chuckles appears in Hawaiian Vacation, he doesn't seem to appear in the other Toy Story Toons episodes so far.
- Chuckles does not appear in Toy Story 4 possibly due to Bud Luckey's death in 2018.