Songfacts®:

• Robbie Williams said that "South Of The Border" was inspired by his move from Stoke-on-Trent to London. Writing on his website, Williams explained: "I whistle along on this track like Roger Whittaker, but the song is about me completely losing the plot and leaving home to move to London."
• This opening line of this song is rumored to be about the British supermodel Kate Moss, who was infamously involved in a cocaine scandal in 2005: "I know a freaky young lady, name of Cocaine Katie." This was changed to "No Shame Katie" in the single version.
  
  Older listeners will remember "Cocaine Katie" from the 1972 Dr. Hook & the Medicine Show hit "The Cover of "Rolling Stone"."
• Williams described this song as "one of the best, so much better than 'Angels.'"
• Directed by Thomas Q Napper, the video for this song was filmed across two days at Bow Studios, London. Williams decided to release "South Of The Border" as a single at the very last minute, hence the largely uneventful video. "We were recording the 'Let Me Entertain You' video the next day, and I just went 'no, we're doing 'South of the Border' as a single,'" he said.
• "South Of The Border" failed to reach the Top 10 in the UK, leading critics to suggest it was the end of Robbie Williams' solo career. On the contrary, his next single, "Angels," catapulted the former member of Take That to international fame.
• This was the third single released from Life Thru a Lens after "Old Before I Die" and "Lazy Days." The song peaked at #14 in the UK, making it Robbie Williams' only single to miss the Top 10 until "Sin Sin Sin" in 2006.