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.
- Rocky Road Blues (1945) – Bill Monroe
- Lost Highway (1949) – Hank Williams
- The Man Who Got Away (1954) – Judy Garland
- Mystery Train (1956) – Elvis Presley
- Not Fade Away (1956) – Buddy Holly
- Cathy’s Clown (1957) – The Everly Brothers
- Right String Baby, Wrong Yo-Yo (1957) – Carl Perkins
- Whole Lotta Loving (1958) – Fats Domino
- Breathless (1958) – Jerry Lee Lewis
- Sleepwalk (1959) – Santo & Johnny
- Will You Love Me Tomorrow (1960) – The Shirelles
- Crying (1961) – Roy Orbison
- I Fall to Pieces (1961) – Patsy Cline
- Do You Love Me? (1962) – The Contours
- Something’s Got a Hold on Me (1962) – Etta James
- You’ve Really Got a Hold on Me (1963) – The Miracles
- Be My Baby (1963) – The Ronettes
- No Particular Place to Go (1964) – Chuck Berry
- Fly Me to the Moon (1964) – Frank Sinatra
- Psycho (1965) – The Sonics
- She’s Not There (1965) – The Zombies
- Papa’s Got a Brand New Bag (1965) – James Brown
- Good Vibrations (1966) – The Beach Boys
- Love Is like an Itching in My Heart (1966) – The Supremes
- Try a Little Tenderness (1966) – Otis Redding
- Go Where You Wanna Go (1966) – The Mamas and the Papas
- For What It’s Worth (1966) – Buffalo Springfield
- Visions of Johanna (1966) – Bob Dylan
- A Day in the Life (1967) – The Beatles
- The End (1967) – The Doors
- All Tomorrow’s Parties (1967) – The Velvet Underground
- Darlin’ Be Home Soon (1967) – The Lovin’ Spoonful
- You Set The Scene (1967) – Love
- I’m A Believer (1967) – The Monkees
- Respect (1967) – Aretha Franklin
- Nights in White Satin (1967) – The Moody Blues
- I Don’t Need No Doctor (1967) – Ray Charles
- All Along the Watchtower (1968) – Jimi Hendrix
- I Put a Spell on You (1968) – Creedence Clearwater Revival
- Sweet Thing (1968) – Van Morrison
- The Weight (1968) – The Band
- Son of a Preacher Man (1969) – Dusty Springfield
- Willie the Pimp (1969) – Frank Zappa (feat. Captain Beefheart)
- He Ain’t Heavy, He’s My Brother (1969) – The Hollies
- Suite: Judy Blue Eyes (1969) – Crosby, Stills & Nash
- Gimme Shelter (1969) – The Rolling Stones
- Hot Fun in the Summertime (1969) – Sly & the Family Stone
- We Can Be Together (1969) – Jefferson Airplane
- Whipping Post (1969) – The Allman Brothers
- Conversation (1970) – Joni Mitchell
- Quem Tem Medo De Brincar De Amor (1970) – Os Mutantes
- The Boxer (1970) – Simon & Garfunkel
- I’ll Be There (1970) – The Jackson 5
- Lola (1970) – The Kinks
- Friend of the Devil (1970) – Grateful Dead
- What Is Life (1970) – George Harrison
- God (1970) – John Lennon
- Layla (1970) – Derek & the Dominos
- Where Do the Children Play (1970) – Cat Stevens
- Northern Sky (1971) – Nick Drake
- Life on Mars (1971) – David Bowie
- I Know (I’m Losing You) (1971) – Rod Stewart
- Without You (1971) – Harry Nilsson
- Me and Bobby McGee (1971) – Janis Joplin
- Will You Love Me Tomorrow (1971) – Carole King
- What’s Going On (1971) – Marvin Gaye
- I Know (1972) – Bonnie Raitt
- And You and I (1972) – Yes
- Supper’s Ready (1972) – Genesis
- Thirteen (1972) – Big Star
- Walk on the Wild Side (1972) – Lou Reed
- Alabama (1972) – Neil Young
- Mona Lisas and Mad Hatters (1972) – Elton John
- Political Science (1972) – Randy Newman
- Ventura Highway (1972) – America
- Children of the Revolution (1972) – T.Rex
- Mr. Bojangles (1972) – David Bromberg
- American Tune (1973) – Paul Simon
- Take Me Home, Country Roads (1973) – Toots & the Maytals
- Ashes Are Burning (1973) – Renaissance
- Search and Destroy (1973) – Iggy & the Stooges
- I’m Straight (1973 version) – The Modern Lovers
- Love, Reign O’er Me (1973) – The Who
- My Old School (1973) – Steely Dan
- Don’t You Worry ‘Bout a Thing (1973) – Stevie Wonder
- Let It Grow (1974) – Eric Clapton
- Too Far Gone (1974) – Emmylou Harris
- Willin’ (1974) – Linda Ronstadt
- Thunder Road (1975) – Bruce Springsteen
- Shine On You Crazy Diamond (1975) – Pink Floyd
- Ten Years Gone (1975) – Led Zeppelin
- Love Is the Drug (1975) – Roxy Music
- What Do You Want from Life? (1975) – The Tubes
- American Girl (1976) – Tom Petty & the Heartbreakers
- Miami 2017 (Seen the Lights Go Out on Broadway) (1976) – Billy Joel
- Jamming (1977) – Bob Marley & the Wailers
- Songbird (1977) – Fleetwood Mac
- Pretty Vacant (1977) – The Sex Pistols
- Sheena Is a Punk Rocker (1977) – The Ramones
- Tenderness on the Block (1978) – Warren Zevon
- Hanging on the Telephone (1978) – Blondie
- Runs in the Family (1979) – The Roches
- Money (1979) – The Flying Lizards
- I’m In Love with You (1979) – Steve Forbert
- Too Much Too Young (1979) – The Specials
- Romeo & Juliet (1980) – Dire Straits
- If I Didn’t Love You (1980) – Squeeze
- Train in Vain (Stand by Me) (1980) – The Clash
- When the World Is Running Down, You Make the Best of What’s Still Around (1980) – The Police
- Our Lips Are Sealed (1981) – The Go-Gos
- The Weakness in Me (1981) – Joan Armatrading
- Senses Working Overtime (1982) – XTC
- Beyond Belief (1982) – Elvis Costello
- Absolutely Sweet Marie (1983) – Jason & the Scorchers
- Add It Up (1983) – Violent Femmes
- Do You Wanna Hold Me? (1983) – Bow Wow Wow
- Naïve Melody (This Must Be the Place) (1983) – Talking Heads
- Show Me (1984) – Pretenders
- I Would Die 4 U (1984) – Prince
- Don’t Worry Baby (1984) – Los Lobos
- Blind Love (1985) – Tom Waits
- Would I Lie to You? (1985) – Eurythmics
- Angel from Montgomery (1985) – Bonnie Raitt & John Prine (live duet)
- In Between Days (1985) – The Cure
- Don’t Toss Us Away (1985) – Lone Justice
- Cloudbusting (1985) – Kate Bush
- Some Journey (1985) – Suzanne Vega
- Scorpio Rising (1985) – 10,000 Maniacs
- Let’s Go (1986) – The Feelies
- Honky Tonk Man (1986) – Dwight Yoakam
- In Your Eyes (1986) – Peter Gabriel
- Baby, It’s You (1987) – Nick Lowe & Elvis Costello
- 4th of July (1987) – X
- With or Without You (1987) – U2
- Sweet Jane (1988) – Cowboy Junkies
- Don’t Let It Break You Down (1988) – Graham Parker
- Lock, Stock & Teardrops (1988) – k.d. lang
- Fight the Power (1988) – Public Enemy
- Ana Ng (1988) – They Might Be Giants
- You Are the Everything (1988) – R.E.M.
- Fisherman’s Blues (1988) – The Waterboys
- Under the Milky Way (1988) – The Church
- Gigantic (1988) – Pixies
- (Believed You Were) Lucky (1988) – ‘Til Tuesday
- Birthday (1988) – Sugarcubes
- I Would Change My Life (1988) – Nanci Griffith
- Flying Cowboys (1989) – Rickie Lee Jones
- Kid Fears (1989) – Indigo Girls
- Deadbeat Club (1989) – The B-52’s
- I’ll Sail This Ship Alone (1989) – The Beautiful South
- Groove Is In the Heart (1990) – Deee-Lite
- Black Boys on Mopeds (1990) – Sinéad O’Connor
- Come As You Are (1991) – Nirvana
- Payphone (1991) – Tribe
- Superman’s Song (1991) – Crash Test Dummies
- Landslide (1992) – Sun-60
- Wild Horses (1992) – The Sundays
- Climb On (A Back that’s Strong) (1992) – Shawn Colvin
- Mr. Jones (1993) – Counting Crows
- 6’ 1’’ (1993) – Liz Phair
- Fade Into You (1993) – Mazzy Star
- Here & Now (1993) – Letters to Cleo
- My Wife Thinks You’re Dead (1993) – Junior Brown
- Cannonball (1993) – The Breeders
- Love Is Everything (1993) – Jane Siberry
- Les Ailes (1993) – Khaled
- Linger (1993) – The Cranberries
- Cherub Rock (1993) – Smashing Pumpkins
- The Wheel (1993) – Rosanne Cash
- Cornflake Girl (1994) – Tori Amos
- Hallelujah (1994) – Jeff Buckley
- Twiggy Twiggy/Twiggy vs. James Bond (1994) – Pizzicato Five
- Undone (The Sweater Song) (1994) – Weezer
- Jing Jing (Firefly) (1994) – Shoukichi Kina
- Violet (1994) – Hole
- Interstate Love Song (1994) – Stone Temple Pilots
- Forgiven (1995) – Alanis Morissette
- Just a Girl (1995) – No Doubt
- Snow Day (1995) – Lisa Loeb
- Crazy Baby (1995) – Joan Osborne
- Wonder (1995) – Natalie Merchant
- Army of Me (1995) – Björk
- Wise Up (1996) – Aimee Mann
- Everyday is a Winding Road (1996) – Sheryl Crow
- Not the Girl You Think You Are (1996) – Crowded House
- History Repeating (1997) – Propellerheads (feat. Shirley Bassey)
- She’s the One (1997) – World Party
- This Is the Day (1997) – Ivy
- Sweet Surrender (1997) – Sarah McLachlan
- To Zion (1998) – Lauryn Hill (feat. Carlos Santana)
- Can’t Let Go (1998) – Lucinda Williams
- Backseat (1998) – Juliana Hatfield
- Push It (1998) – Garbage
- Army (1999) – Ben Folds Five
- She’s A Jar (1999) – Wilco
- Two Points for Honesty (1999) – Guster
- Papa Was a Rodeo (1999) – The Magnetic Fields
- I Know (1999) – Fiona Apple
- Life Is Bad (1999) – Shelby Lynne
- Prom Theme (1999) – Fountains of Wayne
- Waitin’ for a Superman (1999) – The Flaming Lips
- Let’s Save Tony Orlando’s House (2000) – Yo La Tengo
- One Is the Magic # (2000) – Jill Scott
- Bohemian Like You (2000) – Dandy Warhols
- One (2000) – Johnny Cash
- The Galway Girl (2000) – Steve Earle (feat. Sharon Shannon)
- The National Anthem (2000) – Radiohead
- Glitter in their Eyes (2000) – Patti Smith
- Weapon of Choice (2000) – Fatboy Slim
- Sexual Revolution (2001) – Macy Gray
- California Stars (2001) – Billy Bragg & Wilco
- Lovin U (2001) – Alicia Keys
- Someday (2001) – The Strokes
- Gimme a Sign (2002) – Ryan Adams
- Sympathy (2002) – Sleater-Kinney
- Lose Yourself (2002) – Eminem
- In My Place (2002) – Coldplay
- The Golden Age (2002) – Beck
- Get Free (2002) – The Vines
- Lover I Don’t Have to Love (2002) – Bright Eyes
- The Equaliser (2002) – Clinic
- Love Vibration (2003) – Josh Rouse
- Cish Cash (2003) – Basement Jaxx (feat. Siouxie Sioux)
- The Way You Move (2003) – OutKast
- I Just Don’t Know What to Do With Myself (2003) – The White Stripes
- Wake Up (2004) – Arcade Fire
- Babe, You Turn Me On (2004) – Nick Cave & the Bad Seeds
- Sari (2004) – Nellie McKay
- Nanny Nanny Boo Boo (2004) – Le Tigre
- The Book of Right-On (2004) – Joanna Newsom
- Michael (2004) – Franz Ferdinand
- A.S.A. to Accuracy (2004) – KaitO
- Stevie Nix (2005) – The Hold Steady
- Casimir Pulaski Day (2005) – Sufjan Stevens
- Sing Me Spanish Techno (2005) – The New Pornographers
- The Skin Of My Yellow Country Teeth (2005) – Clap Your Hands Say Yeah
- World Spins Madly On (2006) – The Weepies
- Falling Slowly (2006) – Glen Hansard & Markéta Irglová
- Lloyd, I’m Ready to Be Heartbroken (2006) – Camera Obscura
- You Know I’m No Good (2006) – Amy Winehouse
- Born Secular (2006) – Jenny Lewis & the Watson Twins
- Spare-Ohs (2007) – Andrew Bird
- Killing the Blues (2007) – Robert Plant & Alison Krauss
- Breakin’ Up (2007) – Rilo Kiley
- Open Your Heart (2007) – Lavender Diamond
- I Feel It All (2007) – Feist
- Re: Stacks (2007) – Bon Iver
- Creator (vs. Switch and FreQ Nasty) (2008) – Santigold
- Silence (2008) – Portishead
- You! Me! Dancing! (2008) – Los Campesinos!
- Rococo Zephyr (2009) – Bill Callahan
- This Tornado Loves You (2009) – Neko Case
- Hysteric (2009) – Yeah Yeah Yeahs
- Crystalised (2009) – The xx
- Useful Chamber (2009) – Dirty Projectors
- Train Song (2009) – Feist & Ben Gibbard
- Vanderlyle Crybaby Geeks (2010) – The National
- Alpha Shallows (2010) – Laura Marling
- Memory Boy (2010) – Deerhunter
- I Can Change (2010) – LCD Soundsystem
- Monster (2010) – Kanye West
- Powa (2010) – Tune-Yards
- Born Free (2010) – M.I.A.
- Bright Lit Blue Skies (2010) – Ariel Pink’s Haunted Graffiti
- I Saw the Light (2010) – Spoon
- Calamity Song (2011) – The Decemberists
- Cheerleader (2011) – St. Vincent
- Shook Down (2011) – Yuck
- Magic (2011) – Girls
- The Night I Learned How Not to Pray (2012) – Iris DeMent
- Elephant (2012) – Tame Impala
- Kevin’s (2012) – Sharon van Etten
- The Nights of Wine and Roses (2012) – Japandroids
- Laura (2012) – Bat for Lashes
- Acts of Man (2013) – Frightened Rabbit
- Sweet Dreams (2013) – Angel Olsen
- Two Weeks (2014) – FKA Twigs
- Party Police (2014) – Alvvays
- Pedestrian at Best (2015) – Courtney Barnett
- Medieval Warfare (2016) – Grimes
- Real (2016) – Lydia Loveless
- Best to You (2016) – Blood Orange (feat. Empress Of)
- Drugs with Friends (2016) – Car Seat Headrest
- Malamente (2018) – Rosalía
- Nobody (2018) – Mitski
- Night Shift (2018) – Lucy Dacus
- Make Me Feel (2018) – Janelle Monáe
- Almost Had To Start A Fight/In And Out Of Patience (2018) – Parquet Courts
- Your Dog (2018) – Soccer Mommy
- Future Me Hates Me (2018) – The Beths
- Cattails (2019) – Big Thief
- Comme Des Garçons (Like The Boys) (2020) – Rina Sawayama
- Together (2020) – beabadobee
- The Steps (2020) – Haim
- Smile (2021) – Wolf Alice
- Ur Mum (2022) – Wet Leg
- Grandfather please stand on the shoulders of my father… (2023) – Lana Del Rey (feat. RIOPY)
- Right Back To It (2024) – Waxahatchee (feat. M.J. Lenderman)
- Prep School Gangsters (2024) – Vampire Weekend
- This World Is Dangerous (2024) – Hurray for the Riff Raff (w/ Conor Oberst)
At least one song for each year from 1956-2024, with the exception of 2017. Why that one gap?
And the song by The Tubes breaks one of the rules. I don’t own it. But I’m leaving it on the list anyway. It’s a very funny song with many 70s pop culture references.