This song about a cross-dresser is a single from indie pop band The Magnetic Fields tenth studio album Love At The Bottom of The Sea. Their previous three records had no synths on them but Love At features both synthesized and acoustic instruments. The LP was recorded by Magnetic Fields leader Stephin Merritt and Charles Newman at studios in New York City and San Francisco and released on March 5, 2012 by Domino Records in the UK and March 6, 2012 by Merge Records in the US.
The song's music video features Claudia Gonson, who occasionally provides lead vocals for The Magnetic Fields as well as performing the piano and drums. She is also the band's manager. Merritt told Spinner about the clip: "A friend who works at an ad agency approached me about making a video and I said, "Well, we'd love to make a video but our new single is called 'Andrew in Drag.' Good luck." So Claudia went in for 20 minutes and got photographed drinking cognac and standing on our little rotating turntable and that was our basic contribution to the video."