I’ll start with other catagories
Top 5 Books: Slaughterhouse Five, 1984, Pyongyang by Guy Delisle, Where the Wild Things Are, and A Man Without a Country by Kurt Vonnegut (I’m thinking fast)
Top 5 Movies: Brazil, Goodfellas, Raiders of the Lost Ark, The Empire Strikes Back, Monty Python and the Holy Grail
Top 5 Albums: Highway 61 Revisited by Bob Dylan, The Legend of Johnny Cash, Kind of Blue by Miles Davis, American IV by Johnny Cash, and What’s Going On by Marvin Gaye
Songs from stuff in my iTunes.
Beatles Songs: The Long and Winding Road, Lucy in the Sky with Diamonds, A Day in the Life, Strawberry Fields Forever and Yesterday
Johnny Cash: The First Time Ever I Saw Your Face, Satisfied Mind, For the Good Times, Rock Island Line and Sunday Morning Coming Down.
The Rolling Stones: Ruby Tuesday, You Can’t Always Get What You Want, Paint It Black, Gimme Shelter and Sympathy for the Devil. Judging by how many more songs I loved from the Beatles than the Stones, the Beatles win easily. Interesting.
Ella Fitzgerald: Bewitched, Bothered and Bewildered, Miss Otis Regrets, Oh, Lady, Be Good, Someone to Watch Over Me and Bess, You is My Woman Now
Bob Dylan: Visions of Johanna, Leopard Skin Pill Box Hat, Blind Willie McTell, Ballad of a Thin Man, and Just Like a Woman
Jimi Hendrix: Manic Depression, All Along the Watchtower, Are You Experienced?, The Wind Cries Mary and Purple Haze.
Moby: Why Does My Heart Feel So Bad?, South Side, Natural Blues, Porcelain and Now I Let Go. “Play” is in my top 10 all time albums.
Muddy Waters: Mannish Boy, (I’m Your) Hoochie Coochie Man, Rollin’ and Tumblin’ Part I, I Can’t Be Satisfied and Big Leg Woman.
Prince: Let’s Go Crazy, When Doves Cry, Darling Nikki, P Control and Purple Rain
Radiohead: Creep, Karma Police, How to Disappear Completely, The Tourist and Fitter Happier
Simon and Garfunkel: Bridge Over Troubled Water, The Only Living Boy in New York, America, Scarborough Fair (Canticle) and Cecilia.
Those are 11 of my favorite artists, Johnny Cash being an easy #1.