Madness often wrote about the quotidian challenges of life in working-class England. This song is heavy on despair: lead singer Suggs sings from the perspective of a guy beaten down by life, facing another grey, weary day.
The gloom is offset by the video, which is typical Madness goofiness, complete with their famous silly walk.
All seven members of Madness contributed to the songwriting; "Grey Day" was written by multi-instrumentalist Mike Barson.
Like the rest of the album, Madness recorded this in the Bahamas for "tax reasons." Among their neighbors was Clash frontman Joe Strummer. Madness lead singer Suggs recalled in Uncut magazine March 2008: "'Grey Day' was a definite step on for Madness. I remember going to a club with a copy of it and Joe strummer was DJing. I asked him to put this on, because I thought I'd finally done something that he could dig, not just jumping up and down - but he wouldn't play it."
"Grey Day" was first performed by the band when they were known as The North London Invaders. Guitarist Chris Foreman recalled in the same Uncut interview: "We had first done 'Grey Day' three years before, a '60s psychedelic thing with no structure and only a few lyrics." Foreman added: "I remember (co-producer) Alan Winstanley and I bought the album tapes back through customs. I couldn't help laughing at the sticker: These tapes have absolutely no commercial value."
The Isley Brother's song, "Contagious," peaked at #19 on the Billboard Hot 100. This meant that the band of brothers became the first group to score a Top 50 hit in six consecutive decades on the chart.