The four Caravan of Courage trips became one of Hamish & Andy's most loved expeditions as they travelled for up to two weeks in a van meeting locals and having adventures. In 2010, the boys were making their way through Great Britain and Ireland, where they stayed at a haunted castle, went on dates with local girls despite both having girlfriends at home and Hamish conducted an impromptu performance at an Irish Pub.

In 2009, a 19 year old Taylor Swift made her first appearance on the Hamish & Andy show, performing live and agreeing to try a prank call as Swifty Taylor! In this episode the boys also remember Michael Clarke and Lara Bingle's failed energy drink, and Hamish reveals why he was hoping to bump into Chris Martin backstage at a Coldplay concert.

Hamish and Andy are looking at the run sheets from over 2,500 shows across two decades and picking one singular talk break to discuss.