When you think of Jimmy Buffet you probably don’t think of a hardworking businessman — but he’s just that. Crooning songs that paint pictures of a laidback, vacation lifestyle like “Cheeseburgers in Paradise”, Jimmy Buffet launched an entire enterprise off his chilled-out brand. Though he made money from his music and tours, the majority of his cash flow came from his restaurant chains, Margaritaville Café and Cheeseburger in Paradise.
Not only did he own restaurants, but Buffet’s brand can also be seen in convenience and grocery stores everywhere. A true business mogul, Jimmy Buffet also had his own beer label, a casino, and a $1 billion retirement village. And to keep his creative juices flowing he’s written his very own Broadway musical. Who knew Jimmy Buffet was such a hardworking guy?
Jon Stewart — $160 Million
Thirty years into his career and Jon Stewart’s hard work has certainly paid off. Beginning as many comedians do, working stand-up gigs and eventually writing for comedy shows that weren’t his own, Stewart began to make a name for himself in 1993 when he hosted "The Jon Stewart Show" on MTV.
After that initial breakthrough, Stewart continued to host a number of talk shows, including his most famous feature, "The Daily Show." The talk/satire news show helped Stewart accrue a wide-ranging fan base, all of whom were shocked and saddened to hear of his departure from the show in 2015. Stewart chose to leave in order to work on his writing, a decision he most likely does not regret, given the enormous cushion of cash he has to lean on.
Tyra Banks — $90 Million
Beginning her professional career as a supermodel when she was just a teenager, Tyra Banks is business savvy in addition to being beautiful and has spent years growing a multi-media empire. Though she initially struggled to find her professional brand alongside supermodel stars like Naomi Campbell and Gisele Bundchen, Tyra Banks definitely found her niche in the fashion industry after a few years of hard work.
Expanding her career into TV, Banks eventually created the long-running reality TV series, "America’s Next Top Model." Her personality shone through and appealed to American audiences so much that Banks landed her own daytime talk show, "The Tyra Banks Show," in 2005. From that point on, Banks continued her success in the entertainment industry, expanding into music and cosmetics. Truly a self-made woman, Banks was named one of TIME magazine’s most influential people. After looking at her impressive career, it’s certainly not difficult to understand why.
Jerry Springer — $60 Million
Famous for his wild television show, the late great Jerry Springer had an interesting career with a very big paycheck. Mostly known for his sometimes grotesquely dramatic television show, Springer interestingly started off his career as a politician. Jerry Springer got his law degree and practiced in New York where he served as an advisor to John F. Kennedy. He went on to build a political career in Cincinnati.
However, Springer’s career in politics was not as successful as he had hoped and he eventually moved on to the entertainment side of politics by becoming a political commentator and reporter. Here, Springer found his career niche. His talents as a broadcaster eventually lead to what we know Jerry for best, hosting "The Jerry Springer Show." Not so much a talk show as a show of spectacles, Springer’s dramatic television program certainly paid off for him. He sadly passed away in 2023.
George Strait — $310 Million
Heralded for being the “King of Country Music”, George Harvey Strait gained fame for returning the country sound back to its origins when he set off his music in the 1980s. He started things off with a bang when his first single, “Unwound,” became an instant chart-topper after its release in 1981. His next seven albums continued to be hugely successful and repeatedly topped the charts. The success of Strait’s music led to numerous concert tours that helped him earn just over $99 million over the course of three years.
Strait’s impressive and successful music career has not only made him one of the best-selling artists of all time but has actually made him the 12th best-selling artist in United States history. Though he is currently retired on the music front, Strait continues to be a successful and beloved artist. He currently endorses a tequila brand and has embarked on various other business ventures to help pad his already impressive net worth.