We should be calling him Middle-Aged Opportunistic Grifting Asshole, though to be fair, that doesn't roll off the tongue.
Was at a celebrity golf outing where he played a few years back. He showed up right at his tee time because he watched the forecast, assumed it would be rained out and slept in. Made a big deal of slamming a couple of beers (at like 9 a.m., to "calm his nerves"), then played the round in jeans and cowboy boots, alongside some of the greats of the game and some A-list celebrities. He shanked one shot into the gallery and apparently some heckler said something about it. His response: "Let's go get a boombox and you and I can do some rapping. Then we'll see what's what, motherfucker!" Kids everywhere around, too. Pure class.
Nothing says hardass rapper like a white kid dressed like he grew up in a double-wide in Theodore, Alabama, despite having actually grown up on an estate with an apple orchard and a stable outside Detroit, where his dad owned multiple car dealerships.
What was going on in Sheryl Crow's life that she was banging him for a time? Scott Raab was pissed about that.