NEW YORK (CNN/Money) - The breach-of-contract lawsuit filed against Michael Jackson by his former financial adviser has raised questions about the eccentric singer's financial solvency.

The suit may or may not have merit -- Jackson's own countersuit claims he's still very much flush. Regardless, it seems an opportune time to examine the fates of some other famous folks who failed to keep their houses in order. (For more about Jackson, click here.)

To be sure, these stars are mere jesters compared to the King of Pop, whose estate has been said to be worth more than $300 million. Even so, the Gloved One might do well to bear in mind these sad stories.

In the 1980s, M.C. Hammer was the epitome of the rap impresario. His recordings topped the charts, and side business ventures seemed to bear so much fruit that Forbes estimated his 1990 income at $33 million. He went through that money in Hammer time.

The singer's paid entourage was said to number 40 people, he owned at least 17 cars, and he kept a stable of racehorses. (One of his thoroughbreds ran at the Kentucky Derby.) He filed for bankruptcy in April 1996.

With hits like "Smokey and the Bandit" and "Deliverance," good ol' boy Burt was Hollywood's biggest male star in the 1970s, earning up to $5 million a picture. For a while, he seemed everywhere: a high-priced commercial pitchman, network TV star, the glossies' favorite cover boy.

In 1996, the actor declared bankruptcy. Among the 49 creditors listed: the maker of his toupees, whom he owed $122,000.

In the end, Reynolds blamed his public, expensive divorce from his wife Loni Anderson. "I'm paying the third-highest alimony and child support in the world," he told NBC's "Dateline." He added, "And the only two ahead of me are sheiks."

How many athletes get to be America's sweetheart and the progenitor of the country's most-popular hairdo? Throw in a reported $1 million-a-year contract to skate on primetime TV, and Dorothy had it all. Then she spent it.

Her financial troubles spiraled after she bought Ice Capades. By 1994, the skating tour had slid into economic disarray, and Hamill sold it to a group headed by televangelist Pat Robertson. Hamill filed for bankruptcy in 1996.

The diminutive star of TV's "Diff'rent Strokes" was, for a time, the best-paid child actor in America, earning $70,000 per episode.

At the height of his fame, Coleman's net worth was reportedly $18 million. Some of that was spent on legal disputes, including a suit-countersuit imbroglio with his father, who claimed Coleman tried to run him over with a car. Medical expenses – the actor has had two kidney transplants – also piled up.

When he filed for Chapter 7 bankruptcy in 1999, Coleman had been working as a security guard.

Bracco, who received an Oscar nomination for her role as Karen in the movie "Goodfellas," now plays Tony Soprano's shrink. She declared bankruptcy in 1999.

The actress had fought a long custody battle with ex-boyfriend Harvey Keitel, who is her daughter's father. After more than six years of legal squabblings, Bracco told the New York Post, she had spent more than $2 million in legal fees, far exceeding her income.

Remember Anita Bryant? A former Miss America who became a popular singer of wholesome tunes, Bryant was a ubiquitous, highly paid product pitchwoman in the 1970s. She promoted Coca-Cola, Tupperware, Holiday Inn, and, most famously, Florida orange juice.

Her career began to falter in 1977, after she launched a controversial anti-gay rights campaign. The St. Petersburg Times reported that in 1997, Bryant and her husband declared commercial bankruptcy in Arkansas. One creditor, according to the Times: the president of the Anita Bryant fan club, whom the singer was said to owe $3,000.