Settle made his Broadway debut in a strictly limited engagement in Chicago: The Musical, appearing as Billy Flynn from April 19 through June 13. He also had a guest appearance on Law and Order SVU in season 7 as a reporter in the episode Storm. Settle can also be seen as Rufus Humphrey on The CW show Gossip Girl, in which he is the father of Dan and Jenny, two of the main characters. Other past roles include his portrayal of Capt. Ronald Speirs in the HBO mini series Band of Brothers. He also played the part of John in the film Beneath.