Login | Signup

Why We Love… Smilin' Stan S. Stanman

Carl Phillips
Monkey Island, Previously Owned Vessels, Smilin' Stan S. Stanman, Sombrero, Stan, Why We Love


Why We Love… Smilin' Stan S. Stanman

The Monkey Island series has always been filled with strange and colourful characters. It’s one of the many, many reasons I play through them all every so often and relive the pirate-y adventures of Guybrush Threepwood and his eternal struggle against the unrelenting Le Chuck. While I could have spoken about Guybrush or Herman Toothrot, Murray the Talking Skull (who is possibly my favourite character in the game) or even stretched to the “Rubber Chicken With The Pulley In The Middle”, I decided to focus my attention on one of the series’ more eccentric additions to the cast. I’m here today to talk about why we love the most infamous salesman in the Caribbean, Smilin' Stan S. Stanman.

One of only five cast members to appear in all five entries of Monkey Island, Stan has been trying to sell something of the previously-owned variety to someone all his life because, to quote the main man himself, he’d stand on his own head to make you a deal. Along with his mighty fine sombrero, Stan has perhaps the most famous jacket in computer games history, and it’s all down thanks to technical restrictions at the time of programming back in 1990. No matter how fast he moves his arms and no matter how far he moves around the screen, the check-pattern on his jacket always remains stationary. While advances in graphics and textures in gaming would have easily rectified the occurrence in later titles it was kept in as a running gag throughout the series, although newcomers to Monkey Island that had not played the earlier entries cried foul and complained of a graphical glitch on Stan’s costume.

Philistines, the lot of them.

Why We Love… Smilin' Stan S. Stanman

His fast talking, arm flailing, high-intensive sales pitch to anyone that happens to go near him wasn’t always a success but if you could sum him up in one word, it would have to be ‘persistent,’ in every sense of the word.

First encountered on the docks of Melee Island in the original game, Stan was peddling previously owned vessels to any and all that happened to stumble upon him, including a particular wannabe pirate. Along with his snappy attire he would use his marketing spiel, inspired by every used car salesman ever, to ensure he grabbed your attention and it instantly made him a memorable character for me. It would take a little theft before he would actually sell you anything, but he would eventually get his sale and send you off on your merry way to Monkey Island. That’s not to say it would end well for our intrepid salesman, who would learn a valuable lesson before the credits rolled; never try and sell anything to an enraged zombie pirate.


Of course, a punch to the face and being sent halfway across the Caribbean wouldn’t keep him down for long as he would pop up time and time again during Guybrush’s adventures. In the second game he tries his hand at selling previously owned coffins to avoid negative consequences because the dead couldn’t come back and complain. By the time we meet him in the third game he’s trapped in a crypt eating the corpses of the recently dead, but upon being freed by Guybrush and discovering “a new lease on life” he immediately turns the crypt into an office and starts selling Death Insurance, explained as “making sure that if you’re dead, you stay dead.” This ultimately ends badly for Stan who falls victim to insurance fraud thanks to Guybrush, and he eventually closes up shop because too many people are coming back from the dead to claim their policy payouts.

Any other salesperson would call it a day right there, but not our Stan. In the fourth instalment he has set up an emporium from which he sells timeshared real estate, and seemed to have finally got a winner on his hands. His secret? A three hour presentation campaign during which anyone that falls asleep ends up pressured into buying the scheme. Sadly for Stan, Guybrush manages to escape such a fate and is forced to provide him with financial damage coverage of a meal voucher. Between then and the latest entry in the series, Stan decides to stop his salesman ways, at least for a little while, by training to become a lawyer, the funding for which he provided himself by being a part-time exotic dancer.

Whether or not he left his hat on is never revealed.

Why We Love… Smilin' Stan S. Stanman

He may not be one of life’s winners (then again who exactly is in the Monkey Island universe) but his “never say die” attitude, his inventive sales pitches, and his infamous wardrobe makes him a not only a stand out character of the series, but throughout gaming in general. There are many, many reasons gamers young and old should experience the Monkey Island games (and if you haven't, go get the Special Editions, with it out on basically every platform there's now no excuse) but Stan is definitely up towards the top of that list. Should there be another entry to the series I’m sure I won’t be alone in looking forward to seeing what Smilin' Stan S. Stanman has planned for his next business venture.

I’ll sign off by leaving you with a link in the picture below, leading you to an internet classic that is to this day still a fitting tribute to one of gaming’s most beloved entrepreneurs.

Why We Love… Smilin' Stan S. Stanman

Do you agree with Carl's assessment of the Monkey Island's businessman? Perhaps you think he's actually one of the more annoying characters? Got your own favourite moment or quote of the Sombrero'd One? Sign off in the comments below!

Add a comment0 comments


Leave a Trackback from your own site

Email Address:

You don't need an account to comment. Just enter your email address. We'll keep it private.