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 black hair and a shaven face, while Lon has red hair and a beard.
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 not always very sure of himself 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 while Lon is playing around and Ben 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, gently pats Thomas' back, keeps his hand there, and he and Ben compliment Smith for his heroic act. John 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 on shore. Lon, along with Thomas, is amazed by the New World, while Ben is happy just to get off the boat. On shore, 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.
Later on, Thomas notes that John Smith is acting differently. Lon attributes Smith's behavior to the fact that he missed the fight. While pulling up his pants, he points that they can take care of the Indians just like they did the last time they did 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, John 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 pointing 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 tasks the two with finding him. Lon then asks what they should do if they run into 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 the gold.
Later as Smith sneaks out of the camp Ben, Lon, and the other settlers are wondering if Ratcliffe has lied to them and there is no gold or if the Indians have the gold and they'll have to fight them. When Ben and Lon 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, both men agree that some sort of rescue should be attempted. Ratcliffe 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 point out that Smith is free and the Indians don't want to fight. 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. They assist the other settlers in apprehending Ratcliffe. Thomas then orders them and the rest to chain him up and gag him.
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 still in London or came back to Jamestown after John Smith was treated.
Lon makes a cameo in The Hunchback of Notre Dame. He appears during the song "Topsy Turvy" sitting at a table and drinking a beer with another man.
- 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.