Willie Nelson would argue that his marijuana habit isn't the source of any of his life troubles. He's certainly spending a lot of money on staying green, but since his issues with the IRS in the early '90s, he hasn't shown any sign of mishandling finances. He's had at least four arrests for marijuana possession in the last 40 years, but has never been slowed down for much more than a few hours. Each time, he's paid a fine and moved on. Professionally, it's difficult to look at his career and wonder, "What if?" The red-headed stranger has done pretty well for himself.