It would make a little sense: like Bill Murray's character in Groundhog Day, Charlie Sheen is a sarcastic, hedonistic television personality who has seemingly grown tired of a life where he's forced to repeat the same tired punchlines every day. After all, just recently, Sheen eschewed the trappings of his Two and a Half Men paychecks (just two months ago, the star stated that he didn't care whether or not he worked out a deal with CBS) and blew up his marriage (as Sheen famously threatened his wife at knifepoint on Christmas Eve).
He's caught in a cycle that, yes, might be much more lucrative and glamorous than that of a Pittsburgh weatherman, but is still monotonous for a thrillseeker of Sheen's caliber. So instead of seducing women in the local cafe or stealing money, Charlie Sheen is throwing consequence to the wind by burning cash on a criminal attorney to negotiate cigarette and soda privileges on a 15-day prison sentence (with good behavior), stealing a groundhog, and letting it drive his luxury vehicle into a ditch.
OK, fine: Charlie probably just left his keys in the car again, making it easy for some punk to run off with his vehicle. Still, it makes about as much sense as Sheen hijacking a groundhog for a high-speed car chase off a hill, doesn't it?