Eric Weisbard's excellent 2021 book titled Songbooks, looks at works on Popular Music from 1770-2010. A lot of ground is covered, and Weisbard hits pretty much all the classic books that a music fan should have in their personal library. Picking a title and then mentioning other titles similar to his pick, Weisbard makes you want to grab books that you missed. Only misstep is not including the Dave Marsh book I recommend below (Weisbard doesn't like Marsh). While it's a book about music books, by going chronologically, Weisbard tells a story of Popular music.
I've decided to list some of my own favorites that I believe every music fan must own. Most of these are ones Weisbard picked. Also, many of these titles have been updated. But I've included the original year of publication.
My choices:
Anthony Heilbut - Gospel Sound (1971)
Barney Hoskyns - Rip It Up and Start Again (2005)
Bill C. Malone - Country Music USA (1968)
Bob Dylan - Chronicles, Volume 1 (2004)
Bob Stanley - Yeah! Yeah! Yeah! Story of Pop Music (2015)
Charles Hamm - Yesterdays: Popular Song In America (1979)
Charlie Gillett - Sound of the City: The Rise of Rock & Roll (1970)
Chuck Klosterman - Detroit Rock City (2001)
Chuck Eddy - Stairway to Hell: 500 Best Heavy Metal Albums in the Universe (1991)
Dave Marsh - Heart of Rock & Soul: The 1001 Greatest Singles Ever Made (1989)
David Cantwell - Running Kind (2022)
David Cantwell & Bill Friskics-Warren - Heartaches By The Number: Country Music's 500 Greatest Singles
Ellen Willis - Out of the Vinyl Deeps (2011)
Evelyn McDonnell & Ann Powers - Rock She Wrote: Women Write About Rock, Pop & Rap (1995)
Gary Giddins - Visions of Jazz (1998)
Gerri Hirshey - Nowhere to Run: Story of Soul Music (1984)
Greil Marcus - Mystery Train (1975)
Ian MacDonald - Revolution in the Head (1994)
Ira Robbins - Trouser Press Record Guide (1991)
Jeff Chang - Can't Stop, Won't Stop: History of the Hip Hop Generation (2005)
Joel Whitburn - Record Research Chart Books (1973-)
John Morthland - Best of Country Music (1984)
Jon Savage - England's Dreaming (1991)
Legs McNeil & Gillian McCain - Please Kill Me (1996)
Lester Bangs - Psychotic Reactions and Carburetor Dung (1987)
Marissa Moss - Her Country (2022)
Michael Azerrad - Our Band Could Be Your Life (2005)
Nelson George - Death of Rhythm & Blues (1988)
Nick Hornby - High Fidelity (1995)
Nick Tosches - Country (1977)
Nick Tosches - Hellfire (1982)
Patti Smith - Just Kids (2010)
Peter Guralnick - Lost Highway (1979)
Peter Guralnick - Last Train to Memphis: The Rise of Elvis Presley (1994)
Peter Guralnick - Careless Love: The Unmaking of Elvis Presley (1999)
Richard Meltzer - Aesthetics of Rock (1970)
Rob Sheffield - Love Is A Mixtape (2007)
Robert Christgau - Christgau's Record Guide: Rock Albums of the 70's (1981)
Robert Christgau - Christgau's Record Guide: The 80's (1990)
Robert Palmer - Deep Blues (1981)
Rolling Stone Illustrated History of Rock & Roll (1976 + Various Editions)
Rolling Stone Record Guide (1979 + Various Editions)
Tom Moon - 1000 Recordings to Hear Before You Die (2008)