The Real Reason Sinbad Lost Most Of His Money

Sinbad has been many things to many people: An acclaimed comedian. The security detail to the First Kid of these glorious United States. The guy who lost Star Search to the voice of the Crypt Keeper. Not the star of Kazaam, no matter what you think you remember. Blockbuster Entertainment Award Winner.

Then, in 2009, the mononymous '90s comic ran into trouble when he filed for bankruptcy. The case was dismissed when the proper paperwork wasn't filed, so he tried again in 2013. Today, Celebrity Net Worth estimates that Sinbad currently has holdings in the area of $4 million, which, if accurate, would mean that he's pulled off an amazing financial comeback — in total, he claimed in his court case to be in the red for about $11 million just seven years ago.

We know where most of the hits came from — according to NewsOne, more than $8 million of the comedian's debt came in the form of back taxes. But what about the rest?

Those Cosby Show spinoffs can't last forever

From the looks of things, Sinbad's financial difficulties didn't stem from old classics like shady managers or Nicolas Cage castle collections. By his own reckoning, the real problem was optimism.

Speaking to the Huffington Post on the subject of his bankruptcy cases in 2013, Sinbad described working in the entertainment industry in terms that any gig economy employee with a credit card can understand. "I spent money, and I kept thinking, 'I get one more movie and I'll wipe these bills out,' but that movie never came," said Sinbad. "So you owe a million dollars. I can pay that. OK, fines, fees, now you owe two and a half million. 'But I didn't do nothin'!' Now you owe four million."

He went on to state that he never bought into an extravagant lifestyle or big money purchases, which seems largely true — in his court filings, he listed only $131,000 in personal assets.

Sinbad back, Sinbad knees

Stop us if you've heard this one, but it turns out that health care isn't cheap. The bills start to get bigger the older you get, and Sinbad, now 63, has had his fair share of top shelf medical problems over the years.

In the 1970s, the comic had planned to play professional hoops, according to the Sun Gazette. The 6'5 Michigan native even earned a basketball scholarship to the University of Denver, but a knee injury sidelined the aspiring athlete.

Joint damage, as you're probably aware, is the student loans officer of the medical world: it always catches up with you in the end. By the late 2000s, a large frame and an active lifestyle — Sinbad was apparently an avid skier, per an interview with the Estes Park Trail Gazette – had finally taken their toll. In August of 2010, the comedian revealed in a Twitter post that he'd undergone the second of two knee replacement surgeries, the first of which he'd discussed at some length in his special from earlier that year, Where U Been?

Then, in November of 2015, UPI reported that Sinbad was recovering from spinal fusion surgery, a complicated procedure in which two or more vertebrae are welded together. The process reportedly lasted 10 hours. "Thank everyone for their prayers," he later Tweeted. "I shall be back up soon. This surgery was no joke." Perpetually hustling, he was back on stage by January of the following year.

Sinback at it again

Following his health struggles, Sinbad has remained busy, maintaining a tour schedule that would make any comedian jealous, playing multiple shows a night in such bummer locales as Honolulu and Beverly Hills in 2020.

On screen roles have been sparse in recent years. In 2018, he returned to Fox, the network that aired the single season of The Sinbad Show in 1993, for the live-action sitcom Rel starring Lil Rel Howery. The show made it 12 episodes before being cancelled in April of 2019.

Still, if you haven't seen Sinbad lately, there's a chance that you've heard him. In 2013 and 2014, he had a recurring voice role on cult favorite cartoon show Steven Universe playing Mister Smiley, the Beach City Funland mainstay and, in a meta twist, ex-comedian. Then, in 2017, he showed up on the Disney Junior animated series The Lion Guard as Uroho the baboon, a part that lasted two episodes.

Maybe the comedian's shortest lived job, however, was on The Celebrity Apprentice, where he was let go after just two episodes by not-yet-president Donald Trump in 2010. After being "you're fired" by the series host, Sinbad quipped to Oprah that he regretted not having said "you should fire your barber."