- May 5 Arthur Laurents, American playwright (West Side Story: Gypsy), and screenwriter (Rope; Anastasia), dies at 93
- May 7 "Big" George Webley, British broadcaster, composer, bandleader and musician, dies of a heart attack at 53
- May 7 John Walker [Maus], American rock vocalist (Walker Brothers - "The Sun Ain't Gonna Shine (Anymore)"), dies of liver cancer at 67
- May 8 Cornell Dupree, American jazz and R&B session guitarist (Atlantic Records - Aretha Franklin), dies of emphysema at 68
- May 11 (Eugene) "Snooky" Young, American jazz trumpeter who mastered the plunger mute, dies at 92
- May 13 Bernard Greenhouse, American cellist (Beaux Arts Trio), dies at 95
- May 13 Bruce Ricker, American jazz and blues documentarian (The Last of the Blue Devils; Thelonious Monk: Straight, No Chaser), dies at 68
- May 13 Jack Richardson, Canadian record producer (The Guess Who), dies at 81
- May 15 Bob Flannigan, American jazz singer (The Four Freshmen), dies at 84
- May 18 Leonard Kastle, opera composer, librettist, director (The Passion of Mother Ann), and film maker (The Honeymoon Killers), dies at 82
- May 19 Kathy Kirby, English singer (Secret Love), dies at 72
- May 22 Ze'ev Wolfgang Steinberg, Israeli violist and composer, dies at 92
- May 27 Gill Scott-Heron, American writer, poet and singer ("Whitey on the Moon"), dies at 62
- May 27 Jeff Conaway, American actor and singer (Taxi - "Bobby"; Grease - "Kenickie"; Babylon 5 - "Zack"), dies of pneumonia and sepsis at 60
- May 29 Simon Brint, British comic actor, musician, and television composer (French and Saunders; A Bit of Fry & Laurie; Monarch of the Glen), takes his own life at 60
- May 30 Giorgio Tozzi, American operatic bass (dubbed vocals of Emile de Becque for "South Pacific" film), dies at 88
Country Singers
Jazz Singers
Opera Singers
Pop Singers
Rappers
Rock Singers