Crazy Ira and the Douche are played by Matt Besser and Nick Kroll, respectively, who are both former boyfriends of Amy Poehler.
The backstory for Adam Scott's Ben Wyatt character--he had been elected Mayor of his small town when he was still in high school and ended up performing disastrously in that role--was one that the P&R writers strongly considered using in Season 2 as part of Leslie Knope's history.
Ben Wyatt is approximately 35 years old, confirmed that he stated he had never dealt with the mayor term at 18-years-old for 17 years.
Crazy Ira & The Douche's first appearance on the show.