According to Michael Oldfield's 1984 biography of the band, "Southbound Again" was inspired by songwriter Mark Knopfler's "memories of trips to the capital." The lyrics give the impression that he left his Newcastle home after a love affair that had gone bad to seek fame and fortune in the capital, and that he had no money and no place to go. Things didn't happen quite like that. Knopfler worked as a reporter on the Yorkshire Evening Post newspaper in Leeds, and studied for a degree at the city university then moved to the capital where he played in a band called Brewer's Droop, but he also underwent a teacher training course and landed a post as a lecturer at a college in Loughton, Essex, where he played in a band called Café Racers which had a floating line up. Dire Straits actually made their debut as Café Racers, in July 1977. Although money was tight at one point, this is true for most bands when they start out.

"Southbound Again" appears to have been first recorded for a demo in October 1977, for BBC Radio London. The album versions runs to 2 minutes 58 seconds. The song was also released as the B Side of the band's monster debut single "Sultans Of Swing" on the Warner Bros label; in the UK "Eastbound Train" was the B Side. >>