"I'd stand on my head to make you a deal."

Aka:Smilin' Stan
Job:Used ship salesman
Used coffin salesman
Krypt salesman
Cross Salesman
Mutual of Stan
Time Share salesman
Used restaurant supplies salesman
Real Estate salesman
Courtroom souvenir salesman
Appearances: The Secret of Monkey Island
Monkey Island 2: LeChuck's Revenge
The Curse of Monkey Island
Escape from Monkey Island
Tales of Monkey Island
Voice actor:Patrick Pinney
Pat Fraley
Gavin Hammon

Stan is a fast-talking, eccentric salesman in The Tri-Island Area, and regularly made an appearance throughout the series. Whether he liked it or not, he often found himself dealing with Guybrush Threepwood as he went on with his adventures. This has led to Stan in fairly compromising or uncomfortable situations. He harbored no ill-will however, and would gladly sucker deal with Guybrush more often than not.


Stan is a shrewd businessman that will do anything, and everything to clinch a sale, to his detriment at times. He tends to over-hype his wares, and loads them with add-ons or extras, while praising them as real bargains.

He was characterized by his manic arm gestures, oddly patterned shirts, and big mouth.

On the rare occasion that he allowed a customer to speak, he would stand with his hands on his hips and his foot tapped impatiently.

He claimed to be claustrophobic.


Stan is first encountered during The Secret of Monkey Island on Mêlée Island as the proprietor of Stan's Previously Owned Vessels. Previously, he had purchased The Sea Monkey from the chimps who sailed it back from Monkey Island, and would eventually turn around and sell the ship to Guybrush Threepwood when he needed a ship to rescue Elaine Marley from LeChuck. However it turns out that he cheated Guybrush by selling a junk boat for more than what it was worth. After Guybrush recruits all three crew members, he meets him at the docks and starts going on about the boat. He then refuses to sell the boat, however as soon as one of the boat's masts fall off, he changes his mind and runs away telling Guybrush that he can keep it. Near the end of the game, when Guybrush falls into Stan's grog machine after being hit by LeChuck, Stan talks to Guybrush and talks about whether he wants to trade up the boat. As soon as LeChuck arrives there after Guybrush, he tries to make him interested in buying a boat, however LeChuck hits him and he is sent flying away. At the end of the game, he falls into the sea.

During the events of LeChuck's Revenge, Stan moved to Booty Island and opened a Mortuary. He felt it made sense to sell coffins, especially after his failed ship selling venture in Melee Island (as seen in Secret of Monkey Island). Selling to the deceased helped avoid unsatisfied customers coming back to complain.

When he attempted a pitch to Guybrush Threepwood, believing him to be interested in making a purchase, he sat inside one of his finest coffins. He proudly called it 'The Cadillac of Coffins', and demonstrated how roomy and comfortable it was and pointed out the built in cup holder. Threepwood however, shut the lid on him and nailed it down, trapping him inside. The coffin was eventually shipped to Blood Island and buried in one of the crypts there.

According to Curse of Monkey Island, Stan spent three months trapped inside the coffin. He was eventually freed by Guybrush, who also happened to be buried in the same crypt as him. Stan held no malice though, having found that being locked away for so long had given him time to think and reflect. His thoughts led him to begin selling life insurance policies, and promptly set up shop in the crypt that he was released in. He cheerily handed Guybrush his laminated business card, and hoped to deal with him in the future. Guybrush takes out an insurance policy to receive money when he dies, then after Guybrush faked his identity as a member of the Goodsoup family, and he faked his death (again), he retrieved his death certificate and cashed in his insurance policy with the certificate as proof, leaving Stan no other choice but to pay up in gold.

Thanks to Guybrush and possibly other customers that Stan claims to come back as ghosts to cash in on their policies, his Insurance Business went bankrupt and some time before Escape from Monkey Island he moved the Jambalaya Island where he were looking for a job at Ozzie Mandrill Enterprizes but wasn't even offered an interveiw which made him bitter against Ozzie Mandrill, critizing his whole business. Shortly after he started Stan's Time Share Emporium where he sold real estate on Jambalaya Island. Having a "small problem" with the local vermin (which turned out to be quite large in size but never specified which kind of vermin) he had to set his desk outside his Emporium claiming to he wants to be outside on a sunny day when asked by the costumers.

When Guybrush met him again (apperantly forgotten him as Stan at first calls him Bob before Guyrbush reminds him the correct namne) Stan made a sells pitch on his Time Shares, which is so long that Guybrush fell asleep unless he drank the high caffinated Groggacchino. After Guybrush did managed to listen to the whole pitch he said he found it interesting but had to consult Elaine first, Stan understood well and as promised he gave Guybrush a Mega Monkey Coupon for a Mega Monkey Meal at Planet Threepwood. He also offered Guybrush a pamphlet for his Time Shares which he used to blackmail The Grouchy Judge into giving him a fair score at the Diving Contest.


  • Generally only referred to as simply 'Stan', he reveals his full name in Tales of Monkey Island.
  • Stan appears in the opening sequence of Stardew Valley.
  • According to the Director's commentary of Monkey Island 2: LeChuck's Revenge Special Edtion, Stan's jacket pattern remains the same regardless of his movement due to the graphic limitations of the time. In Monkey Island 2 the pattern was kept the same (with the exception of the main color being black) for comedy effect and for all subsequent games thereafter. Ironically, while it was easy to keep the pattern the same in the 2D games, in the 3D games it was much harder to do that due to the nature of textures sticking on a 3D model, so the teams of Escape and Tales struggled to reproduce the effect like in the previous games.

Stan's CareerEdit


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