Lindsay Lohan ($500,000)

Prior to 2007, Lindsay Lohan had it all - money, fame, a hot career and a very bright future. She starred in a slew of box office hits, including Freaky Friday (2003), Mean Girls (2004) and Herbie: Fully Loaded (2005), solidifying herself as a teen idol and a household name.

She was once one of the highest paid actresses in Hollywood and by 2007, Lohan had amassed a net worth of $30 million thanks to endorsements and her acting and music career. However, due to legal troubles, partying, a bad reputation and poor spending habits, Lindsay had squandered her fortune by 2010. With $233,000 in back taxes, $1,000,000 in legal fees, $200,000 in rehab expenses and reckless spending, Lohan's net worth dwindled quickly.

According to Forbes, Lohan blew $7.5 million on hotels, tanning, clothing, partying and luxury cars, in 2007. By 2010, Lindsay had a net worth of $105,000. For the past five years, Lohan has been trying to revitalize her career and fix her reputation.

She now has a net worth of $500,000, but that's a long way from the $30 million fortune she once had.

Heidi Montag & Spencer Pratt ($20,000)
Reality stars Heidi Montag and Spencer Pratt are perhaps the people who have tried the hardest to sustain their reality fame, but they probably should have been focusing on their finances instead.

The two got their start and gained widespread popularity on MTV’s The Hills. After the show wrapped in 2010, they went on to appear in a number of reality shows, including I’m a Celebrity…Get Me Out of Here, Celebrity Wife Swap and Celebrity Big Brother.

Thanks to their reality show careers, they amassed a net worth of $10 million; however, by 2014 Montag and Pratt had squandered it all. In a 2013 interview with In Touch magazine, Pratt confessed, "Every time we’d go out to eat, we’d order $4,000 bottles of wine.

Heidi was going to the mall and dropping $20,000 to $30,000 a day. We thought we were Jay Z and Beyonce". Additionally, Montag dropped nearly $100,000 in 2010 when she underwent 10 plastic surgery procedures in one day.

These days, Heidi and Spencer are now reportedly worth $20,000.

Chris Tucker (-$11.5 million)
Best known for his high pitched, fast talking mouth and starring in the Rush Hour films, Chris Tucker was once one of the highest paid actors in Hollywood.

He earned $25 million for reprising the role of Detective James Carter in the 2007 film Rush Hour 3.

Like many celebrities with poor financial management, Tucker ran into problems with the IRS in 2012 for unpaid taxes from 2001, 2002 and 2004-2006, totaling over $12 million.

Thanks to his debts to the federal government, Tucker has a current net worth of negative $11.5 million.

Sinbad ($-11 million)
Comedian and actor Sinbad, is known for awful films that are memorable due to the fact that many of us get nostalgic about the 90s. Coneheads (1993), First Kid (1996), Jingle All The Way (1997) and Good Burger (1997) are in no way, shape or form Oscar worthy, but Sinbad still made a good living for himself. Despite having consistent work since the early 90s, Sinbad has filed for bankruptcy on two separate occasions, the most recent being in 2013.

He reportedly owes debts of $11 million, $8 million of which stems from back taxes.

In spring of 2013, Sinbad opened up to Oprah Winfrey about his financial situation stating, "I didn’t buy Bentleys. I didn’t live large. I invested in me. I invested in a lot of other people.

I would not change it; I would not go back." Although he has no regrets, Sinbad's investments in himself and other people have left with a net worth of -$11 million.

Kate Gosselin ($50,000)

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number 1 will shock you