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5. Isaac Hayes – The Guy Who Sang Shaft

Another star who made it super-big in the ‘70s was all-time great soul singer Isaac Hayes. He’s another one you might not remember by name, but you’ve definitely heard his biggest hit “Shaft” more times than you know. I mean, “Shaft” even won an Oscar for Best Song (for the movie by the same name, of course). In addition, Hayes was the songwriter for “Soul Man,” one of the most recognizable hits of the 20th century. He was also terrible with money. He mismanaged his own record label, bought everything in sight, and trusted shady advisors all to the tune of a $6 million debt in 1976 and a formal declaration of bankruptcy. At least Hayes figured out his problem. He told Ebony magazine, “I put too much trust in people. I trusted people to take care of business, and I didn’t question them. Being a creative person, I didn’t like to get bogged down in a lot of administrative things. Rather, I hired people who were supposed to be top-notch.”

4. Burt Reynolds – Stupid Alimony…

Poor Burt Reynolds. He seems like such a cool dude, best known for his action roles in ‘70s and ‘80s flicks like Smokey and the Bandit and Sharky’s Machine (which is so awesomely ‘70s, even if it was made in 1981, that you have to find it now on the streaming service of your choice). He was also married to Loni Anderson, who was about as prototypically a hot starlet of her time as you could possibly get. But… Burt and Loni didn’t last. Not forever at least — by 1996, Reynolds, who by then was sort of morphing into an elder statesman of “cool” (check out his performance in Boogie Nights if you don’t believe me) — was divorced from Anderson, paying massive alimony and had also lost a ton of money in a failed Florida restaurant chain. He had to declare bankruptcy and even had foreclosure proceedings begin on his beloved mansion, Valhalla. But Burt is still kicking, kept the house, and is even worth about $5 million these days. Bankruptcy must have been good for him.

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