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Smilin' Stan S. Stanman

Stan TOMI.jpg

Home Island
Species Human
Gender Male
Eye Color
Hair Color Black

Stan (full name: Smilin' Stan S. Stanman) is one of the most frequently recurring characters in the Monkey Island series, having made appearances in all five games. He is a famously sleazy salesman who has run a number of disreputable businesses within the Tri-Island Area and possesses an obsession for money. Though he is never well-liked or particularly successful, Stan is eternally upbeat and confident, forming an odd and unstable friendship with Guybrush Threepwood throughout his various scams and get-rich-quick schemes. However, Stan's love for money and filthy lucre would eventually go to his head as he serves a much more sinister and antagonistic role in Tales of Monkey Island, after realizing just how many of his personal interests could be obtained if he prosecutes Guybrush for his various crimes on Flotsam Island, even going as far as falsifying evidence and witness testimony.


Throughout his numerous cameos in the series, Stan's appearance has remained fairly constant. He is a tall, broad-shouldered man with an overbearing manner. He wears an oversized check jacket and a wide-brimmed hat. When he's talking, he waves his arms about rapidly. When he's listening, he taps his foot impatiently.

His jacket is a recurring visual gag seen throughout the series. Whenever Stan flails his arms around hysterically the check-pattern on his jacket remains stationary. This was originally because of technical restrictions but has since become a standard part of his appearance. (In fact, many people playing Tales of Monkey Island who had not played the earlier games complained that their version had a "glitch", not realizing that this was part of Stan's costume.)

Character history

The Secret of Monkey Island

Stan as seen in The Secret of Monkey Island: Special Edition

When we first meet Stan he is running a used shipyard on Mêlée Island. He has apparently been there some time: all the other characters of the island know him by reputation, and some years ago he sold Herman Toothrot a ship to sail to Monkey Island. With a stolen credit note Guybrush is able to fool Stan into selling him this same ship, now in such a state of disrepair it is literally falling apart.

At the climax of the game LeChuck chases Guybrush to Stan's shipyard. While Guybrush is trapped inside the Grog Machine Stan shows up, greets LeChuck, and launches into his sales pitch. LeChuck punches him into the ocean.

Monkey Island 2: LeChuck's Revenge

In the second game, Stan has moved onto a new business, Stan's Previously-Owned Coffins, located on Booty Island. As he says to Guybrush, he decided to get into a business where unsatisfied customers were less likely to complain. Stan also owns Stan's Kozy Krypts, which has space for burial in a crypt in the Scabb Island cemetery, or, as it is referred to by Stan, the "Scabb Island Internment Park".

As Rapp Scallion is buried inside this crypt, Guybrush needs to steal the key from Stan's shop. To accomplish this he asks Stan to demonstrate the virtues of one of his display coffins, which Stan does enthusiastically, leaping inside to demonstrate the leg room. While Stan is inside Guybrush closes the lid and nails it shut. He then takes the key and leaves Stan shut in the coffin.

The Curse of Monkey Island

While Guybrush is on Blood Island, he gets himself buried in a crypt. He escapes his casket, only to hear a thumping noise from a nearby coffin. When Guybrush opens the coffin, none other than Stan is inside. Surprisingly Stan has no trace of anger towards Guybrush, instead proclaiming that the experience was the best time of his life, giving him plenty of time to think about the things that really matter. He then launches into a fully-formed sales pitch about the need for life insurance, and hands Guybrush a business card. The two of them are still trapped inside the crypt, but Stan reveals that it is one of his Kozy Krypts, and tells Guybrush how to get out.

When Guybrush returns later, Stan has converted the crypt into a functioning office, with his old coffin now serving as a desk. His establishment is named "Mutual of Stan". Guybrush buys a life insurance policy off him for Captain Blondebeard's gold tooth, and cashes it in using a death certificate from the Goodsoup family.

Escape from Monkey Island

Stan gets out of the life insurance business because too many customers were coming back from the dead to claim their policies; he relocates to Jambalaya Island, where he opens Stan's Real Estate Emporium, a business selling time-share real estate. Because Guybrush is able to stay awake throughout his three hour sales pitch (thanks to some grogacchino), Stan rewards him with a coupon for a free Monkey Mug meal at Planet Threepwood. Stan also reveals that he had tried to work for Ozzie Mandrill but Ozzie wouldn't even give him an interview.

Tales of Monkey Island

In "Launch of the Screaming Narwhal", Joaquin D'Oro mentions having purchased a treasure map from a salesman with a plaid jacket and wildly flailing arms. It is later revealed that the treasure map was pre-owned, further reinforcing the implication that the salesman was Stan (whose name was also mentioned as "Smilin' Stan" labeled on his "Young Miss Mini-Bombs - All the Punch of Larger Mini-Bombs, Packed into a Smaller Package for Petite Pirate Hands").

In "The Trial and Execution of Guybrush Threepwood", Stan appears on Flotsam Island, having set up a legal business where the Keelhauler Gazette used to be. He acts as a prosecutor in the case against Guybrush, marking the first time that Stan serves as an antagonist in the Monkey Island series, while selling memorabilia of the trial on the side, one of which Guybrush uses to have one of the charges against him dropped. He also takes part in the trial against LeChuck and the Voodoo Lady, this time working on the defense. The Pox-infected Elaine also acquires a treasure map from him, which—as with D'Oro—no longer leads to any treasure.

Although Guybrush tells Stan "no hard feelings" for the various criminal and civil charges in the courtroom, Guybrush does manage to get a measure of revenge by having a group of vicious moths shred Stan's trademark jacket.

In "Rise of the Pirate God", when Guybrush asks the Treasure Hunter of the Crossroads for the ingredients in the Diet of the Senses, the Treasure Hunter mentions hearing "a tiny voice around here saying 'It's free, dry brush, scrap wood, my trees - try it!'", while unaware that it is actually the voices of the Pyrite Parrots repeating, "It's me. Guybrush Threepwood, Mighty PirateTM!" and thinking that "it might have been ol' Stan implanting subliminal messages in me head to buy some out of season shrubberies".

A Partial List of Stan-Owned Businesses

Main article: Stan-Owned Businesses
  • Stan's Kozy Krypts
  • Stan's Casual Crosses
  • Stan's Previously-Owned Coffins
  • Stan's Previously-Owned Restaurant Supply
  • Stan's Previously Owned Vessels
  • Mutual of Stan
  • Stan's Real Estate Emporium
  • StanTech (sellers of Voodoo-Enhanced Asbestos)
  • Stan's Courtroom Souvenir Emporium

Voice actors

He was voiced by Pat Pinney in The Curse of Monkey Island. Like Elaine Marley, his voice actor changed for his second voiced appearance in the fourth game. In this game he was voiced by Pat Fraley, who also voiced George the Scumm Bar dart player.

In "The Trial and Execution of Guybrush Threepwood", he was voiced by Gavin Hammon. Pinney returned to voice Stan in The Secret of Monkey Island: Special Edition and, more recently, Monkey Island 2 Special Edition: LeChuck's Revenge.


  • Stan is one of only five characters (the others being Guybrush, Elaine, LeChuck and the Voodoo Lady) to have made an appearance in all five Monkey Island games.
  • Stan has a meal named after him at Planet Threepwood: Stan's Budget Baloney Sub. It's four pieces of baloney, ham, and turkey, smothered in three types of cheese, on rye bread. It is not popular.
  • Stan's philosophy "Neither a borrower nor a lender be" is a quote from Shakespeare's Hamlet, Prince of Denmark.
  • In the PS3 version of Tales, after Guybrush finds Stan's Young Miss Mini-Bombs in the Flotsam Jungle in Chapter 1, he can return to the town of Flotsam and repeatedly throw both lit and unlit mini-bombs at Reginald Van Winslow and the Screaming Narwhal prior to repeatedly throwing the Pyrite Parrot atop the Ancient Portal in order to earn the player a "Bats Right, Throws Lame" bronze trophy (a spoof on the idiom "Bats right, throws left") in the "PlayStation Network Trophy Achievements". In Chapter 4, Guybrush can ask Stan if he'd like to browse for the beard toy, the LeChuck doll, and other items and even ask for Stan's jacket both during and after trial in order to earn the player a "Schlock Shopper Supreme" silver trophy.

Game appearances

Memorable Quotes

From Stan

  • "I'd stand on my head to make you a deal."
  • "It's a good thing ol' Stan always keeps a few spare jackets in the back office, or I'd be defending my clients in the altogether! Say, that's not a bad idea... 'Stan S. Stanman, Naked Attorney-At-Law! You've got nothing to hide, and neither does he!'"

About Him

  • "Just when my opinion of the legal profession couldn't get any lower, along comes Stan..." —Guybrush Threepwood