4. Lindsay Lohan

Lindsay Lohan is an American actress, model, producer and recording artist features in films such as Mean Girls, The Canyons and many more.

Lohan has gone through a multiple arrests and was sent to drug rehab.  She owed the government $93,701.57 in 2009, $140,203.30 in 2010 and $56,717.90 in 2011, reports The Vivant. To begin paying back her debts, Lohan signed a deal with the OWN network to star in a reality show about her life.

5. Sinbad

Sinbad is an American stand-up comedian and actor. He became well known in the 1990s starring in the films Necessary Roughness, Houseguest and many more.

In 2009, Sinbad was placed in the top 10 of the 250 worst tax debtors for the state of California. The comedian owed the State $2.5 million in personal income tax. On December 11, 2009, Sinbad filed for Chapter 7 bankruptcy. On February 5, 2010, it was reported that Sinbad put up his 2.5-acre hilltop home for sale in order to ease his tax burdens.

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