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Though he admitted that he isn't a real captain, Captain McCallister has, incompetently, piloted several vessels. On one occasion, he wrecks a cargo ship full of hot pants; on another, in a reference to the Exxon Valdez oil spill, he causes an oil spill by crashing his tanker while drunk. He launches a river raft for Homer, only to have it sink immediately to the bottom. The captain's idea for Mr. Burns' casino involved three ships and fifty "stout men" who would "sail 'round the Horn and return with spices and silk". On several occasions, he acknowledges his incompetence with a depressed, "Yarr, I don't know what I'm doin'". At one time, he tried selling his houseboat to Marge and Homer while they were looking for a new home, and in an obvious nod to Robert Shaw's character in Jaws, starts grappling with a shark when it attacks through the floor. He was apparently a Christian, as he had his ship blessed by Reverand Lovejoy until he learned at least three months later that Lovejoy's blessing the ship didn't count as a blessing since during the three months, his minister license was expired.
As an entrepreneur, McCallister is equally incompetent. His restaurant, The Frying Dutchman, is a failing business venture that does not generate enough income to support its owner. He also once used Homer's bad review for his restaurant despite his hatred of it because it covers up the "D" from the health inspection agency nicely. The captain once appeared as a penniless bum. When seeing Homer and Marge walking Homer's pet lobster at the beach, he approaches them and claims that he runs a "small academy for lobsters". However, when Marge refuses to send the lobster away to "some snobby boarding school", McCallister asks her for spare change instead.
He once mentioned that he has a mother that's made out of wood. He also has at least one son, whom he describes as "the catch of the day".
He has never been shown with a girlfriend and, while it's generally believed that he's not gay, he has hinted to the fact that he has engaged in "situational homosexuality" with his fellow sailors. However, McCallister once took a picture of Patty and Selma in the nude, a picture which he claims to need for "those lonely nights at sea". Though, that being said, Patty and Selma have often been described as very masculine in appearance.
 Behind the Laughter