My cousin Jack decided to make a list of his 60 favorite songs and asked family and friends to do the same. I couldn’t stop at 60, of course.  I ended up with a list of 300 favorite songs.  In order to avoid having the list get even longer, I imposed some (somewhat random) restrictions on myself:

• These are my favorite recordings of songs that I have listened to many times. So, in one case, I have listed the same song recorded by two different artists.
• The songs are not ranked. I have listed them in chronological order.
• I omitted classical, jazz, and blues, although I have many favorite songs/pieces in those genres.
• I limited myself to a maximum of one song per musical artist. This was painful as I could have easily chosen multiple songs for certain artists (Buddy Holly, Beatles, Paul Simon/Simon & Garfunkel, Bob Dylan, Velvet Underground, Elvis Costello, Talking Heads, New Pornographers, Aimee Mann, Wilco, Radiohead, etc.), but I felt the limitation was necessary to keep the list a reasonable length.
• The list is limited to songs I had in my iTunes library in October 2026. If I used to own the album, CD, or tape of the song in the past or only heard it on the radio, I didn’t list it (e.g., Runaround Sue, American Pie, Alice’s Restaurant).
• These are not necessarily my favorite artists – there are numerous artists I like very much but for whom I could not identify a favorite song (Jason Isbell, Fairport Convention, Kendrick Lamar, Beach House, etc.).
• Ask me the same question next year, and I might come up with an entirely different list.

Here is the list.  Feel free to use the comment section to share your favorite songs.

1. Lost Highway (1949) – Hank Williams
2. The Man Who Got Away (1954) – Judy Garland
3. Mystery Train (1956) – Elvis Presley
4. Not Fade Away (1956) – Buddy Holly
5. Cathy’s Clown (1957) – The Everly Brothers
6. Right String Baby, Wrong Yo-Yo (1957) – Carl Perkins
7. Whole Lotta Loving (1958) – Fats Domino
8. Breathless (1958) – Jerry Lee Lewis
9. Sleepwalk (1959) – Santo & Johnny
10. Will You Love Me Tomorrow (1960) – The Shirelles
11. Crying (1961) – Roy Orbison
12. I Fall to Pieces (1961) – Patsy Cline
13. Do You Love Me (1962) – The Contours
14. Something’s Got a Hold on Me (1962) – Etta James
15. You’ve Really Got a Hold on Me (1963) – The Miracles
16. Be My Baby (1963) – The Ronettes
17. No Particular Place to Go (1964) – Chuck Berry
18. Fly Me to the Moon (1964) – Frank Sinatra
19. Psycho (1965) – The Sonics
20. She’s Not There (1965) – The Zombies
21. Papa’s Got a Brand New Bag (1965) – James Brown
22. Good Vibrations (1966) – The Beach Boys
23. Love Is like an Itching in My Heart (1966) – The Supremes
24. Try a Little Tenderness (1966) – Otis Redding
25. Go Where You Wanna Go (1966) – The Mamas and the Papas
26. For What It’s Worth (1966) – Buffalo Springfield
27. Visions of Johanna (1966) – Bob Dylan
28. A Day in the Life (1967) – The Beatles
29. The End (1967) – The Doors
30. All Tomorrow’s Parties (1967) – The Velvet Underground
31. Darlin’ Be Home Soon (1967) – The Lovin’ Spoonful
32. You Set The Scene (1967) – Love
33. I’m A Believer (1967) – The Monkees
34. Respect (1967) – Aretha Franklin
35. Nights in White Satin (1967) – The Moody Blues
36. I Don’t Need No Doctor (1967) – Ray Charles
37. All Along the Watchtower (1968) – Jimi Hendrix
38. I Put a Spell on You (1968) – Creedence Clearwater Revival
39. Sweet Thing (1968) – Van Morrison
40. The Weight (1968) – The Band
41. Son of a Preacher Man (1969) – Dusty Springfield
42. Willie the Pimp (1969) – Frank Zappa (feat. Captain Beefheart)
43. He Ain’t Heavy, He’s My Brother (1969) – The Hollies
44. Suite: Judy Blue Eyes (1969) – Crosby, Stills & Nash
45. Gimme Shelter (1969) – The Rolling Stones
46. Hot Fun in the Summertime (1969) – Sly & the Family Stone
47. We Can Be Together (1969) – Jefferson Airplane
48. Whipping Post (1969) – The Allman Brothers
49. Conversation (1970) – Joni Mitchell
50. Quem Tem Medo De Brincar De Amor (1970) – Os Mutantes
51. The Boxer (1970) – Simon & Garfunkel
52. I’ll Be There (1970) – The Jackson 5
53. Lola (1970) – The Kinks
54. Friend of the Devil (1970) – Grateful Dead
55. What Is Life (1970) – George Harrison
56. God (1970) – John Lennon
57. Layla (1970) – Derek & the Dominos
58. Where Do the Children Play? (1970) – Cat Stevens
59. Northern Sky (1971) – Nick Drake
60. Life on Mars (1971) – David Bowie
61. (I Know) I’m Losing You (1971) – Rod Stewart
62. Without You (1971) – Harry Nilsson
63. Me and Bobby McGee (1971) – Janis Joplin
64. Will You Love Me Tomorrow (1971) – Carole King
65. What’s Going On (1971) – Marvin Gaye
66. I Know (1972) – Bonnie Raitt
67. And You and I (1972) – Yes
68. Supper’s Ready (1972) – Genesis
69. Thirteen (1972) – Big Star
70. Walk on the Wild Side (1972) – Lou Reed
71. Alabama (1972) – Neil Young
72. Mona Lisas and Mad Hatters (1972) – Elton John
73. Political Science (1972) – Randy Newman
74. Ventura Highway (1972) – America
75. Children of the Revolution (1972) – T.Rex
76. Mr. Bojangles (1972) – David Bromberg
77. American Tune (1973) – Paul Simon
78. Take Me Home, Country Roads (1973) – Toots & the Maytals
79. Ashes Are Burning (1973) – Renaissance
80. Search and Destroy (1973) – Iggy & the Stooges
81. I’m Straight (1973 version) – The Modern Lovers
82. Love, Reign O’er Me (1973) – The Who
83. My Old School (1973) – Steely Dan
84. Don’t You Worry ‘Bout a Thing (1973) – Stevie Wonder
85. Let It Grow (1974) – Eric Clapton
86. Too Far Gone (1974) – Emmylou Harris
87. Willin’ (1974) – Linda Ronstadt
88. Thunder Road (1975) – Bruce Springsteen
89. Shine On You Crazy Diamond (1975) – Pink Floyd
90. Ten Years Gone (1975) – Led Zeppelin
91. Love Is the Drug (1975) – Roxy Music
92. What Do You Want from Life (1975) – The Tubes
93. American Girl (1976) – Tom Petty & the Heartbreakers
94. Miami 2017 (Seen the Lights Go Out on Broadway) (1976) – Billy Joel
95. Jamming (1977) – Bob Marley & the Wailers
96. Songbird (1977) – Fleetwood Mac
97. Pretty Vacant (1977) – The Sex Pistols
98. Sheena Is a Punk Rocker (1977) – The Ramones
99. Tenderness on the Block (1978) – Warren Zevon
100. Hanging on the Telephone (1978) – Blondie
101. Runs in the Family (1979) – The Roches
102. Money (1979) – The Flying Lizards
103. I’m In Love with You (1979) – Steve Forbert
104. Too Much Too Young (1979) – The Specials
105. Romeo & Juliet (1980) – Dire Straits
106. If I Didn’t Love You (1980) – Squeeze
107. Train in Vain (Stand by Me) (1980) – The Clash
108. When the World Is Running Down, You Make the Best of What’s Still Around (1980) – The Police
109. Our Lips Are Sealed (1981) – The Go-Gos
110. The Weakness in Me (1981) – Joan Armatrading
111. Senses Working Overtime (1982) – XTC
112. Beyond Belief (1982) – Elvis Costello
113. Absolutely Sweet Marie (1983) – Jason & the Scorchers
114. Add It Up (1983) – Violent Femmes
115. Do You Wanna Hold Me? (1983) – Bow Wow Wow
116. This Must Be the Place (Naïve Melody) (1983) – Talking Heads
117. Show Me (1984) – Pretenders
118. I Would Die 4 U (1984) – Prince
119. Don’t Worry Baby (1984) – Los Lobos
120. Blind Love (1985) – Tom Waits
121. Would I Lie to You? (1985) – Eurythmics
122. Angel from Montgomery (1985) – Bonnie Raitt & John Prine (live duet)
123. In Between Days (1985) – The Cure
124. Don’t Toss Us Away (1985) – Lone Justice
125. Cloudbusting (1985) – Kate Bush
126. Some Journey (1985) – Suzanne Vega
127. Scorpio Rising (1985) – 10,000 Maniacs
128. Let’s Go (1986) – The Feelies
129. Honky Tonk Man (1986) – Dwight Yoakam
130. In Your Eyes (1986) – Peter Gabriel
131. Baby, It’s You (1987) – Nick Lowe & Elvis Costello
132. 4^th of July (1987) – X
133. With or Without You (1987) – U2
134. Sweet Jane (1988) – Cowboy Junkies
135. Don’t Let It Break You Down (1988) – Graham Parker
136. Lock, Stock & Teardrops (1988) – k.d. lang
137. Fight the Power (1988) – Public Enemy
138. Ana Ng (1988) – They Might Be Giants
139. You Are the Everything (1988) – R.E.M.
140. Fisherman’s Blues (1988) – The Waterboys
141. Under the Milky Way (1988) – The Church
142. Gigantic (1988) – Pixies
143. (Believed You Were) Lucky (1988) – ‘Til Tuesday
144. Birthday (1988) – Sugarcubes
145. I Would Change My Life (1988) – Nanci Griffith
146. Flying Cowboys (1989) – Rickie Lee Jones
147. Kid Fears (1989) – Indigo Girls (w/ Michael Stipe)
148. Deadbeat Club (1989) – The B-52’s
149. I’ll Sail This Ship Alone (1989) – The Beautiful South
150. Groove Is In the Heart (1990) – Deee-Lite
151. Black Boys on Mopeds (1990) – Sinéad O’Connor
152. Come As You Are (1991) – Nirvana
153. Payphone (1991) – Tribe
154. Superman’s Song (1991) – Crash Test Dummies
155. Landslide (1992) – Sun-60
156. Wild Horses (1992) – The Sundays
157. Climb On (A Back that’s Strong) (1992) – Shawn Colvin
158. Mr. Jones (1993) – Counting Crows
159. 6’ 1’’ (1993) – Liz Phair
160. Fade Into You (1993) – Mazzy Star
161. Here & Now (1993) – Letters to Cleo
162. My Wife Thinks You’re Dead (1993) – Junior Brown
163. Cannonball (1993) – The Breeders
164. Love Is Everything (1993) – Jane Siberry
165. Les Ailes (1993) – Khaled
166. Linger (1993) – The Cranberries
167. Cherub Rock (1993) – Smashing Pumpkins
168. The Wheel (1993) – Rosanne Cash
169. Cornflake Girl (1994) – Tori Amos
170. Hallelujah (1994) – Jeff Buckley
171. Twiggy Twiggy/Twiggy vs. James Bond (1994) – Pizzicato Five
172. Undone (The Sweater Song) (1994) – Weezer
173. Jing Jing (Firefly) (1994) – Shoukichi Kina
174. Violet (1994) – Hole
175. Interstate Love Song (1994) – Stone Temple Pilots
176. Forgiven (1995) – Alanis Morissette
177. Just a Girl (1995) – No Doubt
178. Snow Day (1995) – Lisa Loeb
179. Crazy Baby (1995) – Joan Osborne
180. Wonder (1995) – Natalie Merchant
181. Army of Me (1995) – Björk
182. Wise Up (1996) – Aimee Mann
183. Everyday is a Winding Road (1996) – Sheryl Crow
184. Not the Girl You Think You Are (1996) – Crowded House
185. History Repeating (1997) – Propellerheads (feat. Shirley Bassey)
186. She’s the One (1997) – World Party
187. This Is the Day (1997) – Ivy
188. Sweet Surrender (1997) – Sarah McLachlan
189. To Zion (1998) – Lauryn Hill (feat. Carlos Santana)
190. Can’t Let Go (1998) – Lucinda Williams
191. Backseat (1998) – Juliana Hatfield
192. Push It (1998) – Garbage
193. Army (1999) – Ben Folds Five
194. She’s A Jar (1999) – Wilco
195. Two Points for Honesty (1999) – Guster
196. Papa Was a Rodeo (1999) – The Magnetic Fields
197. I Know (1999) – Fiona Apple
198. Life Is Bad (1999) – Shelby Lynne
199. Prom Theme (1999) – Fountains of Wayne
200. Waitin’ for a Superman (1999) – The Flaming Lips
201. Let’s Save Tony Orlando’s House (2000) – Yo La Tengo
202. One Is the Magic # (2000) – Jill Scott
203. Bohemian Like You (2000) – Dandy Warhols
204. One (2000) – Johnny Cash
205. The Galway Girl (2000) – Steve Earle (feat. Sharon Shannon)
206. The National Anthem (2000) – Radiohead
207. Glitter in their Eyes (2000) – Patti Smith
208. Weapon of Choice (2000) – Fatboy Slim
209. A Place Called Home (2000) – PJ Harvey
210. Sexual Revolution (2001) – Macy Gray
211. California Stars (2001) – Billy Bragg & Wilco
212. Lovin U (2001) – Alicia Keys
213. Someday (2001) – The Strokes
214. Gimme a Sign (2002) – Ryan Adams
215. Sympathy (2002) – Sleater-Kinney
216. Lose Yourself (2002) – Eminem
217. In My Place (2002) – Coldplay
218. The Golden Age (2002) – Beck
219. Get Free (2002) – The Vines
220. Lover I Don’t Have to Love (2002) – Bright Eyes
221. The Equaliser (2002) – Clinic
222. Love Vibration (2003) – Josh Rouse
223. Cish Cash (2003) – Basement Jaxx (feat. Siouxie Sioux)
224. The Way You Move (2003) – OutKast
225. I Just Don’t Know What to Do With Myself (2003) – The White Stripes
226. Wake Up (2004) – Arcade Fire
227. Babe, You Turn Me On (2004) – Nick Cave & the Bad Seeds
228. Sari (2004) – Nellie McKay
229. Nanny Nanny Boo Boo (2004) – Le Tigre
230. The Book of Right-On (2004) – Joanna Newsom
231. Michael (2004) – Franz Ferdinand
232. A.S.A. to Accuracy (2004) – KaitO
233. Stevie Nix (2005) – The Hold Steady
234. Casimir Pulaski Day (2005) – Sufjan Stevens
235. Sing Me Spanish Techno (2005) – The New Pornographers
236. The Skin of My Yellow Country Teeth (2005) – Clap Your Hands Say Yeah
237. World Spins Madly On (2006) – The Weepies
238. Falling Slowly (2006) – Glen Hansard & Markéta Irglová
239. Lloyd, I’m Ready to Be Heartbroken (2006) – Camera Obscura
240. You Know I’m No Good (2006) – Amy Winehouse
241. Born Secular (2006) – Jenny Lewis & the Watson Twins
242. Spare-Ohs (2007) – Andrew Bird
243. Killing the Blues (2007) – Robert Plant & Alison Krauss
244. Breakin’ Up (2007) – Rilo Kiley
245. Open Your Heart (2007) – Lavender Diamond
246. I Feel It All (2007) – Feist
247. Re: Stacks (2007) – Bon Iver
248. Creator (2008) – Santigold (feat. Switch & Freq Nasty)
249. Silence (2008) – Portishead
250. You! Me! Dancing! (2008) – Los Campesinos!
251. Rococo Zephyr (2009) – Bill Callahan
252. This Tornado Loves You (2009) – Neko Case
253. Hysteric (2009) – Yeah Yeah Yeahs
254. Crystalised (2009) – The xx
255. Useful Chamber (2009) – Dirty Projectors
256. Train Song (2009) – Feist & Ben Gibbard
257. Vanderlyle Crybaby Geeks (2010) – The National
258. Alpha Shallows (2010) – Laura Marling
259. Memory Boy (2010) – Deerhunter
260. I Can Change (2010) – LCD Soundsystem
261. Monster (2010) – Kanye West (feat. Jay-Z, Rick Ross, Nicki Minaj & Bon Iver)
262. Powa (2010) – Tune-Yards
263. Born Free (2010) – M.I.A.
264. Bright Lit Blue Skies (2010) – Ariel Pink’s Haunted Graffiti
265. I Saw the Light (2010) – Spoon
266. Calamity Song (2011) – The Decemberists
267. Cheerleader (2011) – St. Vincent
268. Shook Down (2011) – Yuck
269. Magic (2011) – Girls
270. The Night I Learned How Not to Pray (2012) – Iris DeMent
271. Elephant (2012) – Tame Impala
272. Kevin’s (2012) – Sharon van Etten
273. The Nights of Wine and Roses (2012) – Japandroids
274. Laura (2012) – Bat for Lashes
275. Acts of Man (2013) – Frightened Rabbit
276. Sweet Dreams (2013) – Angel Olsen
277. Two Weeks (2014) – FKA Twigs
278. Party Police (2014) – Alvvays
279. Pedestrian at Best (2015) – Courtney Barnett
280. Medieval Warfare (2016) – Grimes
281. Real (2016) – Lydia Loveless
282. Best to You (2016) – Blood Orange (feat. Empress Of)
283. …Drugs with Friends… (2016) – Car Seat Headrest
284. Malamente (2018) – Rosalía
285. Nobody (2018) – Mitski
286. Night Shift (2018) – Lucy Dacus
287. Make Me Feel (2018) – Janelle Monáe
288. Almost Had To Start A Fight/In And Out Of Patience (2018) – Parquet Courts
289. Your Dog (2018) – Soccer Mommy
290. Future Me Hates Me (2018) – The Beths
291. Cattails (2019) – Big Thief
292. Comme Des Garçons (Like The Boys) (2020) – Rina Sawayama
293. Together (2020) – beabadobee
294. The Steps (2020) – Haim
295. Smile (2021) – Wolf Alice
296. Ur Mum (2022) – Wet Leg
297. Grandfather please stand on the shoulders of my father… (2023) – Lana Del Rey (feat. RIOPY)
298. Right Back To It (2024) – Waxahatchee (feat. M.J. Lenderman)
299. Prep School Gangsters (2024) – Vampire Weekend
300. This World Is Dangerous (2024) – Hurray for the Riff Raff (w/ Conor Oberst)