Game show from the past 15 years?
There was a game show where the host would walk up to random people on the street and ask them a trivia question. If they answered correctly, he would hand them cash ($20?) and just walk away. I believe it was in California, often by the beach. It aired on a cable channel like Spike TV, TBS, etc. I don't think it was on the Game Show Network. I believe the host was a stand-up comedian and was husky. Years after the show had ended, I saw him in something else and he had lost a lot of weight. I distinctly recall him in a commercial where he was a rodeo clown.
It was not Street Smarts with Frank Nicotero.