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In 2006, Baldwin played a villainous thug in the television film Jesse Stone: Night Passage.In August 2007, Baldwin returned to television, when CMT cast him in Ty Murray's Celebrity Bull Riding Challenge, one of nine celebrities cast.From January to March 2008, Baldwin appeared on Donald Trump's Celebrity Apprentice on NBC.He finished fifth out of the 14 celebrity contestants.He revealed the tattoo to Cyrus at a book signing in Nashville on November 10, 2008.Baldwin and his wife defaulted on paying 4,488.36 on their mortgage.In June 2012, a jury sided with Costner and awarded Baldwin no damages.In March 2013, Baldwin pleaded guilty to failing to file income taxes for the years 2008, 20.
As of April 18, 2009, the show aired on 213 stations and in more than 400 cities across the US, and worldwide on Sirius 161 and XM 227. He is known for appearing in films, including Born on the Fourth of July (1989), Posse (1993), Threesome (1994), The Usual Suspects (1995), Bio-Dome (1996) and The Flintstones in Viva Rock Vegas (2000).He also starred in the television series The Young Riders (1989–92), and as himself in the reality shows Celebrity Big Brother 7 (UK) and Celebrity Apprentice.Baldwin is the youngest brother of actors Alec, Daniel and William, sometimes collectively known as the "Baldwin brothers".
In high school, Baldwin participated on the varsity wrestling team, along with William.
He failed to win many fans and was evicted on January 22, 2010, becoming the fourth housemate to be evicted.