When his first owner Daisy owned him, Chuckles was happy. Ever since Lotso became evil and took over Sunnyside, he became downcast, 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 a picture of him, he gives his first genuine smile in years.
Chuckles is a clown doll with blue wilted hair. His hair used to be straightened up when 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.
Sometime before the events of Toy Story 3, Chuckles was owned by Daisy 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 Lotso being 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 gone to eat lunch and accidentally left Lotso, Chuckles, and Big Baby on the ground. After lunch, because Daisy had a fun-filled day and a good lunch, she fell asleep. Because of this, he (Chuckles), Lotso, and Big Baby were accidentally left behind. But, because Lotso believed that Daisy would return for them one day, they waited for quite some time for her to return. After waiting for a long time, and one rainy day, the trio finally gave up waiting for Daisy, so they went to her if she wouldn't go to get them.
When they finally got to Daisy's, 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. Chuckles had tried to comfort 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 Van 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). At Bonnie's house, Chuckles would warn Bonnie's toys about Lotso and the cruel system of Sunnyside.
Chuckles is first introduced while Woody is at Bonnie's house. When Woody mentions Sunnyside, Bonnie's other toys become surprised to see that he has escaped 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 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 him smiling made by Bonnie. This caused him to smile, presumably for the first time in years. He is also shown smiling as he and the other toys gather around to enjoy Buzz and Jessie perform a pasodoble to the Spanish version of the song "You've Got a Friend in Me" in front of them.
In Hawaiian Vacation, Chuckles is seen when Woody announces to the toys that Bonnie has left on vacation for her winter break. 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.
- 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, he became depressed and only frowned with his hair down (the latter 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 his voice likely changed over time. However, it is unknown as to why Chuckles had a silly, high-pitched, clownish voice (performed by Bob Peterson) when he is mostly heard speaking using animator Bud Luckey's primary gruff, reserved, elderly-sounding voice. It could be that his voice sounds more silly when he's happy, and gruffer when he's sad.
- In Toy Story 3, even though Chuckles never smiled around Woody and Bonnie's toys after his horrible time at Sunnyside, when he goes into toy mode, he actually smiles when the humans are present. Though if one looks closely in the scene where the toys meet Bonnie's toys, Chuckles can be seen smiling when he is greeted by Mrs. Potato Head.
- It seemed likely that Chuckles refused to be a lackey of Lotso's during his self-proclaimed role in the movie.
- When Chuckles got broken, even though this is never said in the film, it may be possible that it was not by one of the kids at Sunnyside. Lotso may have been the one that broke Chuckles (like how he broke Chatter Telephone). When he lifts his right armpit while explaining he was broken, you can see the stitching on the right side of his body.
- Although Chuckles appears in Hawaiian Vacation, he hasn't appeared in the other Toy Story Toons episodes so far.
- Chuckles didn't appear in Toy Story 4. It's unknown why he didn't appear in the film, it was likely due to his voice actor, Bud Luckey's death, but he probably still lives in Bonnie's house but not in her room with the rest of her toys.