- “You know something, Robin? I was just wondering: are we good guys or bad guys? You know, I mean, uh, our robbing the rich to feed the poor.”
- ―Little John questioning Robin Hood
Nothing is known regarding Little John's past. However, he is the best friend and sidekick to Robin Hood. Little John appears to be more cautious than Robin Hood and often reminds his friend of the potential consequences of his plans. However, Little John is shown to be extremely loyal to his friend, going so far as to threaten Prince John when the tyrant sentences Robin to death for treason. When not participating in one of Robin's plans, Little John is shown to be fairly laid back, while also offering good advice to Robin.
Like Robin Hood, Little John is talented with disguises. His two disguises seen include a gypsy fortuneteller, and a Duke called Sir Reginald. He later impersonates the Sheriff of Nottingham. When fighting, he is seen using various weapons, including a quarterstaff, and a dagger. He appears to have some familiarity with archery, as he is seen using one during the jailbreak sequence.
He is shown to be a skilled fighter since he punched the Sheriff with ease and defeated the Rhino guards.
Little John is often seen alongside Robin Hood, first escaping from the Sheriff of Nottingham and his posse. Despite the successful escape, Little John worries about being captured and hanged. He later attempts to cite a law against robbing royalty to try to get out of robbing Prince John. However, he assists Robin in the robbery of Prince John while disguised as a gypsy. While Robin is in the royal coach with the Prince, Little John remains outside and steals gold from a large chest as well as the gold hubcaps of the coach.
Later on, he is seen in a hideout he shares with Robin, trying to encourage the lovesick Robin to propose to Maid Marian, whom Robin is in love with. He then gets upset with Robin for not paying attention when he was supposed to be tending to the fire, annoyingly saying "Aw man, you burnt the chow!" Robin seems unconcerned about the blackened food and dismisses the suggestion of engagement, claiming his outlaw status would not fit life with Marian. Little John somewhat sarcastically remarks for Robin to think of something, for he sure is not going to impress Marian with his cooking abilities (as John annoying adds spices to try to salvage his dinner). When Friar Tuck arrives at the hideout and delivers news about Prince John's archery tournament with a winning prize being a kiss from Marian, Little John notes that Robin could win it "standing on his head" but also fears that the Prince's guards, as well as the Sheriff, will be at the tournament.
Little John is next seen at Prince John's archery tournament, reminding Robin, who has disguised himself as a stork to enter the tournament, that he must fool the Sheriff of Nottingham. While Robin participates in the tournament, Little John, disguised as a nobleman named Sir Reginald, Duke of Chutney, consorts with Prince John. After Robin is unmasked and captured, Little John is instrumental in helping Robin escape execution by threatening Prince John's life if Robin is not released.
Later, Little John is in his hideout with the citizens of Nottingham (including Friar Tuck and his mice), where they surprise Robin and Marian after the couple return from their moonlight stroll. During a celebration honoring the newly-engaged couple, Little John plays his song "The Phony King of England" on his lute and dances with Lady Kluck.
Much later, Little John assists in a jailbreak to rescue the citizens of Nottingham, including Friar Tuck, who is sentenced to hang at dawn. Robin retrieves the jail key and passes it to Little John, who then goes into the jail. He frees the citizens while Robin climbs up to the royal treasury to reclaim the taxes that Prince John had taken from them. Little John later impersonates the Sheriff to facilitate their escape and pulls a cart loaded with all the citizens of Nottingham, intent on taking them to Sherwood Forest. When Robin is trapped in the castle, and forced to jump in the moat to escape, Little John is seen watching from the forest with Skippy. He, like Prince John, believes Robin to be dead, as the Sheriff's posse had been shooting at Robin. He is overjoyed to see that Robin has survived his escape from the castle, after initially believing the latter had been killed.
After King Richard returns, Little John is pardoned alongside Robin. He drives the coach containing newlyweds Robin Hood and Marian and allows Skippy to join them.
In some episodes, he is seen sitting with Robin Hood next to Baloo and Bagheera after a cartoon ends.
In "Ask Von Drake", he is seen sitting at a table with Lady Kluck and a puppy from One Hundred and One Dalmatians and is later seen in the background during "The Ludwig Von Drake Song" when Ludwig von Drake names off Lumière and Cogsworth.
At the beginning of the theme song, he is seen inside at the entrance talking and laughing with Baloo.
In the Enchanted Forest, a human Little John is part of Robin Hood's band of Merry Men who pilfer money from the wealthy for the needy. After successfully pulling a stealing heist on the road, everyone rejoices at their campsite. A new recruit, Will Scarlet, procures a large chest of treasures and is accepted into their group. Will suggests their next destination should be Maleficent's castle. Robin Hood accepts only after being convinced the rewards are worth the risk, as Maleficent is currently away, and the hordes of gold inside the castle will be enough to feed many poor villagers. Once they break in, Robin Hood emphasizes that only the gold will be taken and nothing else. Following the success, they once again regroup at camp but are interrupted by the booming voice of Maleficent, who demands the return of a stolen item or suffer the consequences. Angrily, Robin Hood calls the thief among them to step forward, but no one does. Unknown to Little John, Will previously took a looking glass from the castle, and later escapes during the night. ("Forget Me Not")
Little John is portrayed by Jason Burkart in the third season. He turns out to live in the Enchanted Forest, exactly in the old mansion of Rumplestiltskin where he comes to help Neal and Mulan, with his friend and leader, Robin Hood. The way whether he was spared by the curse remains a mystery. A possible explanation is that Robin Hood, the Merry Men, and himself were spared by the curse by the spell of Cora, as it was the case for Mulan, Aurora, and Prince Phillip. Little John is also the protector of Roland, the son of Robin Hood, and the deceased Marian.
- Little John bears a lot of resemblance to Baloo in appearance, personality, and voice since they are both voiced by Phil Harris. However, Little John is smarter, more serious, and more responsible than Baloo. Also, many of his animations are recycled Baloo animations.
- Paul Winchell, Bing Crosby and Ray Bolger were both considered to voice Little John.