"Walking Down Madison" is a song by Kirsty MacColl featuring Aniff Cousins, released by Virgin Records on 7 May 1991 as the lead single from her third studio album, Electric Landlady.

The song was written after MacColl was searching for a new musical direction but instead found writer's block; she tried writing things and asked others to try but it failed to click.

Despite it being the first song he had written after the split of the Smiths, he had kept it to one side for his own solo record after the presentation of some of his new material resulted in his friends stealing the tracks.

It also features rapper Aniff Cousins,[2] who came to MacColl's attention after she heard the single "Black Whip" by his band Chapter and the Verse.

[6] In a 1991 interview with Daily Record, MacColl commented on the song's social message, "I was in New York and became aware of the contrast between the enormous skyscrapers – these huge symbols of power and wealth – and people sleeping in shop doorways.

It shows both a smartly dressed MacColl walking down Madison amidst smartly dressed business men during the daytime and a more-scruffily-dressed MacColl with women sleeping rough, the "beaming boy from Harlem with the air force coat" (which is mentioned in the lyrics of the song), a man with a knife on the A-train and other assorted characters at night whilst Londonbeat dance.

[9] Upon its release, Music & Media noted the song's display of the "new styled MacColl" and described it as "match[ing] modern dance material as supplied by acts like Massive Attack or the Banderas".

[11] Steve Stewart of the Aberdeen Press and Journal awarded four out of five stars and wrote, "A bit of everything thrown in here – dance beat, rap, screeching guitar and vocal harmonies.