Jimmy’s first appearance on The Tonight Show with Jay Leno was June 23^rd 2003 (Burbank, California). In later interviews Jimmy mentioned how nice Jay had been and that he’d been invited back to Jay’s home to see his collection of classic cars.

In relation to this show Jimmy said (on Friday Night With Jonathan Ross) that he’d been really nervous but his nerves had been settled when Cameron Diaz accidentally flashed him. The full story is around 5 minutes 30 on this link.

He must’ve made a good impression as, on July 18^th, he was at Montreal’s Just For Laughs Festival and was asked to provide a live report. The Globe and Mail reported that the “wickedly funny Irishman” (their description) provided one of 3 live feeds for Jay’s show.

Video below is from June 23^rd.