Stanley DeSantis was born in Roslyn, New York, on July 6, 1953. One of six children, his family moved to Chicago, Illinois, after his father, who was in the clothing business, went bankrupt. DeSantis graduated from high school in 1971.
After studying acting at Illinois Wesleyan University, DeSantis made his acting debut at Chicago’s Drury Lane Theater. He later moved to New York, where he attended NYC Film School and first started designing and selling t-shirts out of his apartment.
His first big success with t-shirts came in the 1970s and was inspired by The Wizard of Oz. The t-shirt featured a now-infamous “Surrender Dorothy” design featuring the phrase written across the sky by the handle of the Wicked Witch of the West’s broomstick. His iconic take on pop culture turned truck stop t-shirts into fashion statements.
Side Hustle Turns Day Job
It is not unusual for actors to have a side job or business to help provide income between acting jobs, and DeSantis was no exception. In addition to a t-shirt company called Passing4Sane, he owned Bubbletown, a novelty soap company.
Despite appearing onstage in theaters, he would not appear on screen until 1978, a year after moving to Los Angeles, when he played the role of a law student on The Paper Chase. He would go on to star in more than forty other television and film productions, including Ed Wood, The Birdcage, and Boogie Nights.
But the clothing venture was so popular that by 1980, DeSantis worked full-time with his clothing business and acted part-time. He was a millionaire by the time he reached his thirtieth birthday. Within four years, in 1987, his profits would triple that amount, and he would go on to hold licenses for pop culture entertainment such as The Simpsons, Star Wars, and South Park, to name a scant few.
DeSantis sold the shirts in popular stores of the time, such as JC Penney, a major department store, and Spencers, a popular novelty gift store in shopping malls. In addition to his t-shirts, which were often related to Hollywood films, he designed graphics for the costumes for the 1984 Summer Olympics, held in Los Angeles.
From Recession to the Penthouse
In the early 1990s, America suffered a recession. While other businesses were losing revenue, his t-shirt business helped actor Stanley DeSantis keep a shirt on his back. Logos that parodied the grim economic times became wildly popular because, as he put it, “The history of America is when things get tough our sense of humor gets us through.”
Although DeSantis had retired from acting to live a comfortable lifestyle in a Los Angeles penthouse, a friend pulled him back into the industry in 1991. By the mid-90s, DeSantis was able to pick and choose auditions for the parts he wanted. His t-shirts had given him enough of a financial cushion that he could act for the love of it, not for a paycheck. His Van Nyes-based company raked in around $18 million per year in sales by the mid-to-late 90s.
DeSantis held his own against Hollywood A-listers such as Laura Linney, with whom he became friends. He escorted her to the 2002 Emmy Awards, and she thanked him in her acceptance speech when she won the award for “Outstanding Lead Actress in a Miniseries or a Movie” for the film “Wild Iris.”
A Lasting Legacy
In 2005, DeSantis died due to cardiac arrest in Los Angeles, California, and was survived by his three sisters and multiple nieces and nephews. He was never married and had no children.
A DeSantis shirt featuring the Genie from Disney’s Aladdin sold for $6,000 in 2020. Although he is no longer with us, the DeSantis legacy of iconic t-shirts will last for many future generations. While not all of his shirts sell for thousands of dollars each, many currently sell for as much as ten times or more than their original value online and in brick-and-mortar vintage clothing shops.