Ben and Lon are two of the settlers that travel to the New World with the Virginia Company. The two appear to be close friends (despite Ben occasionally insulting Lon) and are usually seen together. Both are familiar with the reputation of John Smith and are fairly loyal to him. Ben has long black hair and a shaven face, while Lon has red hair and a beard and moustache.
Both are pleasant and cheerful men, although Lon is notably more enthusiastic and fun-loving and often tries to see things through rose-colored glasses, whereas Ben will not suffer fools gladly.
Lon also shows that he's somewhat insecure as he doesn't often speak in confidence, such as when he simply asks Ratcliffe how long they were going to keep digging, unlike Ben who confronts Ratcliffe momentarily to tell him that they're "slaving away" and not getting anywhere. Lon also demonstrates this when, after Ben kicks him for playing around and tells him to get back to work, Lon timidly says, "Come on, Ben. It's just a little fun."
Ben and Lon first appear as two of the crew members on the ship that is headed towards the New World. The two meet Thomas, a young man who wants to seek his fortune, and discuss the fact that the legendary John Smith would be on the voyage. Ben notes John's reputation for fighting savages; in his view, he cannot fight Indians without him.
During the voyage, Ben and Lon are seen tying off cannons during a storm. When Thomas falls overboard, Smith rescues him in a daring move. Ben openly calls Smith crazy, but he and Lon assist in the rescue by pulling Smith and Thomas back to the ship with a rope.
Back on the ship, Lon drapes a dry towel over Thomas, tells him he's a "lucky lad", gently pats Thomas' back, keeps his hand there, and he and Ben compliment Smith for his heroic act. Smith replies that they would surely do the same for him as he wrings out Thomas' hat and places it back on Thomas; Ben and Lon hesitate for a moment but quickly answer in the affirmative.
At the New World, Ben and Lon are some of the first settlers to go onshore. Lon, along with Thomas, is amazed by the New World, while Ben is happy just to get off the boat proven when he says "It can look like Ratcliffe's knickers for all I care. Just as long as we're off this stinking boat!" Onshore, Ben and Lon are tasked with digging for gold. When they fail to find anything, Ben and Lon begin to complain, with Ben becoming mildly confrontational. However, they are interrupted when Governor Ratcliffe's dog, Percy, discovers some Indians to which they mistakenly believe are ambushing them and rush to grab muskets and fight. Ratcliffe shoots an Indian named Namontack in the leg; Ben tries to kill the wounded Namontack with his gun, but is stopped from finishing the job by Kocoum who kicks Ben away.
A few days later, Thomas notes that Smith is acting differently and being unusually quiet. Lon attributes Smith's behavior to the fact that he missed the fight and was upset about it. While pulling up his pants, he points out that they can take care of the Indians just like they did the last time and picks up a pickaxe. Using it to impersonate a musket, he begins singing, "We shot ourselves an injun, or maybe two or three." while pretending to shoot. At this, Smith appears pained while Thomas seems to be the only one who finds the performance amusing. Ben, who is in a very bad mood, kicks Lon from behind and tells him, "Alright ya howlin' nutter, get to work." Lon complains to Ben that he was just trying to have fun. Ben sarcastically agrees to point out that they've been searching for gold for hours without any food while Ratcliffe is in his tent, "happy as a clam." Later, Ben and Lon are found napping when Ratcliffe comes looking for Smith. Ben and Lon realize that he has disappeared, Ben telling Lon, "Aye, your singing must have scared him off." Ratcliffe replies, "Well then, go get him for heaven's sake!" Lon then asks, "What if we run into the Indians?" Ratcliffe, not even trying to hide his annoyance, tells him, "That's what guns are for. Now arm yourselves and get moving." Ben and Lon eventually arrive at the glade of Grandmother Willow, who is helping to hide Smith, as well as Pocahontas. Grandmother Willow is able to spook the two men, and the two quickly flee, with Ben insisting, "He's a big lad, he can take care of himself!"
When Smith returns to camp, Lon and Ben reveal that they were looking for him, but before Smith can answer them, Ratcliffe appears asking Smith about his whereabouts. John Smith gives the excuse that he was scouting the terrain. When Ratcliffe reveals that he plans to fight the Indians, Smith protests, much to the surprise of Ben and Lon. Smith reveals that he met an Indian (Pocahontas), that he had food, and that there was no gold in Virginia. When Ben and Lon hear that there is no gold, they start to question Ratcliffe, but Ratcliffe insists that the Indians have it.
Later, as Smith sneaks out of the camp, Ben and the other settlers are sitting around a campfire, discussing what Smith has said earlier. The former, still having some degree of loyalty to Ratcliffe, refuses to believe he would drag them across the ocean for nothing or that Kocoum's group attacked them for no reason (although it was because they attacked first, and the Indian warriors were only doing so in retaliation), but Lon, as well as some of the others, are beginning to suspect that Ratcliffe has misled them. Ben and Lon later hear Thomas calling for help, Lon tells Thomas to settle down and asks what's wrong. When Thomas tells them that John has been captured, Ben tells the others, "Thomas is right. We've got to do something." The other men agree as Ratcliffe comes out, takes advantage of the situation, and prepares for an all-out war against the Indians.
The next morning, Ben and Lon are among the soldiers preparing to fight. They are surprised when John is released thanks to Pocahontas. Though Ratcliffe wishes to start the war anyway, both Ben and Lon join Thomas in standing up to Ratcliffe starting with Ben who tells Ratcliffe, "They don't want to fight." When Ratcliffe tells them it's a trick, Lon joins them as they begin to suspect that John was right about him. They witness Ratcliffe (who was aiming for Chief Powhatan) shoot Smith, and believe that it was intentional, now realizing that Smith was right after all and they shouldn't have listened to Ratcliffe in the first place. He played them like puppets. They assist the other settlers in apprehending Ratcliffe. Thomas then orders them and the rest to chain him up and gag him.
After this, Thomas is seen taking supplies to them. Ben asks Thomas if John will be okay, to which Thomas tells him, "Sooner he gets back to England, the better." Lon puts a hand on Thomas' shoulder and tells him, "Well, let's hope the wind is with him." Thomas then questions on the ship's readiness to sail back to England. Ben answers in the affirmative that it was almost ready, they just had to load "the last bit of cargo". He then smiles as the scene changes to show the men taking a chained and gagged Ratcliffe back to the ship.
At the end of the film, it is revealed that Lon plans to stay behind in Jamestown with Thomas to carry out the settlement, as he is heard wishing good luck to Smith, who must return to England for medical treatment. Presumably, Ben decides to return to London to get Smith to get cured, as he is seen rowing the wounded Smith back to the ship which leaves for London.
Neither Ben nor Lon are seen or mentioned in the sequel, Pocahontas II: Journey to a New World. Thus, it is unknown what happened to them. Presumably, Lon is still carrying out the settlement with Thomas, while Ben is either still in London or has come back to Jamestown after John Smith was treated.
When the player is on the seventh page, if they scroll to the right, Ben and Lon can be found digging for gold. If the player clicks on them, they will start to dig. Ben will accidentally shovel dirt on Lon's head. Lon and Ben then turn to face each other. Lon shakes his fist at Ben while saying, "You watch where you're shoveling?" The two then turn back around and resume their original positions.
- Ben was originally supposed to be English, however, attempting a London accent hurt Billy Connolly's throat so the actor chose to use his native accent instead and Ben became Scottish.
- Connolly's other Disney animated film character King Fergus in Pixar's 2012 film Brave is entirely Scottish.
- Both Lon and Ben observe John Smith's execution with other English colonists in this animated film. In real life, there were no Englishmen observing the incident when Pocahontas rescued Smith. Smith was the only Englishman in Chief Powhatan's village.
- While Ben is native Scottish, Lon on the other hand, is purely English.
- In 1996, Billy Connolly went on to play the Narrator and Billy Bones in Muppet's Treasure Island.
- It's possible that Ben was named for either Benjamin Best who was one of the actual Jamestown settlers or Ben Jonson who wrote her story in his comedy The Staple of News.
- Despite being English, Lon's name is actually of Spanish Origin and means "noble, ready".
- After his part in Pocahontas, Mel Gibson invited Billy Connolly to play King Robert of Scotland in Braveheart the same year.
- In 1994, Joe Baker played Barnard in Dumb and Dumber and Ben Weatherstaff in The Secret Garden.