Oh, lawdy... I gotta have me a swing at this

Anvil - X Men's tattoo artist.
Schro - S.F. 49'ers water boy.
SimplyRed - Lawn mower salesman.
PowerofCheese - Mike Myers' sidekick in "The Love Guru, Part II."
BrkEatr - Wine taster for Night Train.
Herronm - Stunt glider pilot.
MikeKoz - Marital aid salesman.
Timmay - Lifeguard at a wading pool.
Bootedbear - Scouting that house prior to breaking in.
Time2Shine - Roller skating instructor.
GASlick - High school lacrosse coach.
Tyler - 3 card monte dealer.
Champ007 - Sleeps on the beach in Hawaii.
Marsh1000 - Balloon artist.
FR8TRAIN - Professional guppy fisherman.
Buuckkweet - Tree surgeon.
Warhawk - Showing us how to milk a cow.
Skiking - Does drive-by's with a paint ball gun.
SlickEric - Roadie for Right Said Fred.
JohnMont - Taste tester for Vlasic pickles.