200 Pop Songs That Made Me Cry
/My (very personal) list of 200 favorite pop vocal recorded performances (as estimated on 31 December 2024) …that I’m still, to this day, not sick of!
Admittedly, I started this list two years ago, as a compendium to a list of “Favorite Albums” (that was the catalyst for several people to stop speaking to me, or so I imagined), but I soon became paralyzed by the idea, because the more songs I put on the list, the more it made clear to me just how, both, limited my “taste” was… and limitless the sheer number of songs one could choose from. That is to say, it’s a misguided, foolish, and insane (not that that matters) task.
SO, I quickly abandoned it—only to pick it up again a couple of days ago (due to end-of-year desperation?) but decided to limit the scope to: Pop Vocals “that made me cry”—not because they’re sad (though some of them are), but because they are beautiful and one of kind. And… leaving out: instrumental jazz, show tunes, blues, folk, R&B for the most part, hip hop, bluegrass, etc.… and the 99.999 plus percent of music that I’m ignorant about. But I’ve included bubblegum, punk, and country (three sides of the same coin). I realize it’s pretty light on the last 50 years, and even lighter on anything before I was born (1960). At any rate, not even attempting to be relevant, or reflective of what’s “great” or “important”—this is just a “winging it,” off the top of my head (I know in a week or so I’ll realize I forgot my second-fav-all-time song!) of what’s been delighting me (to the point of tears) these last few years—and leaving out, entirely unfairly, stuff I’m sick of, for whatever reason (could just be that I heard it too much ).
I sometimes get suckered into those mainstream online media clickbait “Greatest Songs” lists, which usually seem like a combination of some enormous editorial consensus coupled with a few odd choices afforded the poor bastards doing the work. (Or else, these days, entirely AI generated.) For the most part, those lists make me feel like I hate music—just due to the prevalence of songs that I wish I never had to hear again in my life. So, I thought I’d make my own list, which reflects who I am, song-wise (a sentimental white man who was a teenager in 1973, with a weakness for nostalgia but an attraction to eccentricity)—but as “lists” go, this might be the most ridiculous, as it’s likely anyone else making a similar list will not have a single similar crossover entry as mine—which means… no common ground. But that’s also what makes it, for me, fun—the extreme subjectivity. Please see it as a way to celebrate people’s differences, and don’t get angry about “obvious” exclusions (or inclusions) and possibly skip by the songs here that you feel similarly about, and hopefully get reminded of some music you’ve liked but have forgotten about, and if you happen to see a song you’re not familiar with, if it’s possible to find somewhere, give an open-minded listen and maybe discover something to love.
As far as the order—yes, they’re “in order”—just because that’s even more ridiculous, still.
—Randy Russell 12.31.24
200 Anywhere I Lay My Head – Tom Waits – Rain Dogs (1985)
199 Love Hurts – Roy Orbison – Crying (1962)
198 I’m Your Man – Leonard Cohen – I’m Your Man (1988)
197 Perfect Day – Lou Reed – Transformer (1972)
196 Jack and Jill – Tommy Roe – single (1969)
195 Security Joan – Donald Fagen – Morph the Cat (2006)
194 Your Mind Is on Vacation – Mose Allison – I Don’t Worry About a Thing (1962)
193 Bodies – Sex Pistols – Never Mind the Bollocks, Here’s the Sex Pistols (1977)
192 She’s Making Friends, I’m Turning Stranger – Purple Mountains – Purple Mountains (2019)
191 Baby Baby – The Vibrators – single (1977)
190 Bohemian Rhapsody – Queen – A Night at the Opera (1975)
189 Little Hitler – Nick Lowe – Jesus of Cool (1978)
188 Changes – David Bowie – Hunky Dory (1971)
187 Jealous Again – Black Flag – Jealous Again (EP) (1980)
186 Memories – Leonard Cohen – Death of a Ladies’ Man (1977)
185 Angels Don’t Fly – George Jones – Along Came Jones (1991)
184 Downtown – Petula Clark – single (1964)
183 From an Airplane – Iris Dement – The Trackless Woods (2015)
182 Sultans of Swing - Dire Straits – Dire Straits (1978)
181 Melody Hill – The Archies – single B-side (1969)
180 Alison – Elvis Costello – single (1977)
179 Crying – Roy Orbison – Crying (1962)
178 Nobody’s Fault but Mine – Led Zeppelin – Presence (1976)
177 Cocksucking Blonde – Stephen Yerkey – Confidence, Man (1994)
176 Neat Neat Neat – The Damned – single (1967)
175 Any Major Dude Will Tell You – Steely Dan – Pretzel Logic (1974)
174 Fade into You – Mazzy Star – So Tonight That I Might See (1993)
173 Little Fat Baby – Sparklehorse – It’s a Wonderful Life (2001)
172 Older Guys – The Flying Burrito Brothers – Burrito Deluxe (1970)
171 Dog Food – Iggy Pop – Soldier (1980)
170 Deanna – Nick Cave and the Bad Seeds – Tender Prey (1988)
169 Glisan Street – Richmond Fontaine – Winnemucca (2002)
168 Without You – Harry Nilsson – Nilsson Schmilsson (1971)
167 Duty – Nils Lofgren – Nils Lofgren (1975)
166 Grasshopper – The Mamas & the Papas – People Like Us (1971)
165 Strawberry Fields Forever – The Beatles – single (1967)
164 Alright, Yeah – Robyn Hitchcock – Moss Elixir (1996)
163 Heaven – Talking Heads – Fear of Music (1979)
162 Caligari’s Mirror – Pere Ubu – Dub Housing (1978)
161 Big Wheels – Electric Light Orchestra – Out of the Blue (1977)
160 Bird of Paradise – Michael Franks – Abandoned Garden (1995)
159 Lost in Space – Luna – Penthouse (1995)
158 Donna – David Johansen – David Johansen (1978)
157 Suspicious Minds – Elvis Presley – single (1969)
156 Rock & Roll Doctor – Little Feat – Feats Don’t Fail Me Now (1974)
155 4th of July, Asbury Park (Sandy) – Bruce Springsteen – The Wild, the Innocent & the E Street Shuffle (1973)
154 Idiot Wind – Bob Dylan – Blood on the Tracks (1975)
153 I’ll Never Get Out of This World Alive – Hank Williams – single (1952)
152 Birth to Death – Tulip Sweet and Her Trail of Tears – Cry (2002)
151 Good Vibrations – The Beach Boys – single (1966)
150 King of Hearts – Lucinda Williams – Happy Woman Blues (1980)
149 Wish You Were Here – Pink Floyd – Wish You Were Here (1975)
148 Lawrence of Euphoria – Alexander “Skip” Spence – Oar (1969)
147 Stranger in a Strange Land – Leon Russell – Leon Russell and the Shelter People (1971)
146 The Moon – Cat Power – The Greatest (2006)
145 Brown Sugar – The Rolling Stones – Sticky Fingers (1971)
144 Rose Parade – Elliott Smith – Either/Or (1997)
143 September Gurls – Big Star – Radio City (1974)
142 Up the Junction – Squeeze – Cool for Cats (1979)
141 King Midas in Reverse – The Hollies – single (1967)
140 The Caves of Altamira – Steely Dan – The Royal Scam (1976)
139 The Grand Tour – George Jones – The Grand Tour (1974)
138 Earthquake – Leona Naess – Comatised (2000)
137 Cyclotron – Electric Eels – single (B-side) (1978)
136 Love Letter – Nick Cave and the Bad Seeds – No More Shall We Part (2001)
135 By the Time I Get to Phoenix – Isaac Hayes – Hot Buttered Soul (1969)
134 I Can’t Stay Mad at You – Skeeter Davis – Let Me Get Close to You (1964)
133 In the Neighborhood – Tom Waits – Swordfishtrombones (1983)
132 Nevertheless – Brian Jonestown Massacre – Bravery Repetition and Noise (2001)
131 Purple Haze – The Jimi Hendrix Experience – single (1967)
130 Pink Moon – Nick Drake – Pink Moon (1972)
129 What Comes After Certainty – Bill Callahan – Shepherd in a Sheepskin Vest (2019)
128 37 – Devo – Hardcore Devo Volume 2 (1991)
127 Mama Told Me (Not to Come) – Three Dog Night – It Ain’t Easy (1970)
126 I’m Comin’ Home – Richard Harris – Slides (1972)
125 Lay Lady Lay – Bob Dylan – Nashville Skyline (1969)
124 Deacon Blues – Steely Dan – Aja (1977)
123 Personality Crisis – New York Dolls – New York Dolls (1973)
122 I Can’t Explain – The Who – single (1964)
121 Blue Arrangements – Silver Jews – American Water (1998)
120 Hospital – The Modern Lovers – The Modern Lovers (1976)
119 He’s Everywhere - Sammi Smith – Help Me Make It Through the Night (1970)
118 Rock ’n’ Roll with Me – David Bowie – Diamond Dogs (1974)
117 Build Me Up Buttercup – The Foundations – Build Me Up Buttercup (1968)
116 We Can Talk – The Band – Music from Big Pink (1968)
115 Avant Gardener – Courtney Barnett – single (2013)
114 How Can You Mend a Broken Heart – Al Green – Let’s Stay Together (1972)
113 Spooky – Classics IV – Spooky (1968)
112 Barstool Blues – Neil Young and Crazy Horse – Zuma (1975)
111 Inner City Blues (Make Me Wanna Holler) – Marvin Gaye – What’s Going On (1971)
110 Goo Goo Muck – The Cramps – Psychedelic Jungle (1981)
109 It’s Too Late – Carole King – Tapestry (1971)
108 Playboys – Mono – Formica Blues (1997)
107 Sad Song - Lou Reed – Berlin (1973)
106 Memorabilia – Donald Fagen – Sunken Condos (2012)
105 Sexy MF – Prince & the New Power Generation – Love Symbol (1992)
104 Ballad of Big Nothing – Elliott Smith – Either/Or (1997)
103 Smooth Operator – Sade – Diamond Life (1984)
102 Itinerant Child – Ian Dury & the Blockheads – Mr. Love Pants (1998)
101 Members Only – Sheryl Crow – The Globe Sessions (1998)
100 Now Love Has No End – Michael Franks (with Valerie Simpson) – Barefoot on the Beach (1999)
99 I Wanna Be Your Dog – The Stooges – The Stooges (1969)
98 Ocean (Outtake) – Velvet Underground – Loaded (1970/1997)
97 Sometimes Like a River (Loving You) – Joy of Cooking – Closer to the Ground (1971)
96 You Can’t Put Your Arms Around a Memory – Johnny Thunders – So Alone (1978)
95 Superstar – The Carpenters – single (1971)
94 Public Animal #9 – Alice Cooper – School’s Out (1972)
93 Space Oddity – David Bowie – single (1969)
92 Tiny Dancer – Elton John – Madman Across the Water (1971)
91 Animal Speaks – 15-60-75 – Jimmy Bell’s Still in Town (1976)
90 Walk On By – Isaac Hayes – Hot Buttered Soul (1969)
89 Trojan Curfew – Stephen Malkmus – Stephen Malkmus (2001)
88 $1000 Wedding – Gram Parsons – Grievous Angel (1974)
87 Going Going Gone – Richard Hell and the Voidoids – Destiny Street (1982)
86 Alone 4 Love – Tulip Sweet and Her Trail of Tears – Cry (2002)
85 The Mess Inside – The Mountain Goats – All Hail West Texas (2002)
84 Drunken Angel – Lucinda Williams – Car Wheels on a Gravel Road (1998)
83 Groove Me – King Floyd – single (1970)
82 Lola – The Kinks – Lola Versus Powerman and the Moneygoround, Part One (1970)
81 Sunday Mornin’ Comin’ Down – Kris Kristofferson – Kristofferson (1970)
80 Sam Stone – John Prine – John Prine (1971)
79 Stay with Me – Faces – single (1971)
78 12 Varieties of Worms – Frank Kogan – Stars Vomit Coffee Shop (1986)
77 Let It Be Me – Bob Dylan – Self Portrait (1970)
76 She’s Got You – Patsy Cline – single (1962)
75 Digging Song – Cate Le Bon – Me Oh My (2009)
74 Make Me Smile – Chicago – single (1970)
73 Loving Cup – Rolling Stones – Exile on Main St. (1972)
72 Time Has Come Today – The Chambers Brothers – The Time Has Come (1967)
71 Cold, Cold Heart – Hank Williams with His Drifting Cowboys – single (1951)
70 Albuquerque – Neil Young – Tonight’s the Night (1975)
69 Alice – Mott the Hoople – The Hoople (1974)
68 Sideshow by the Seashore – Luna – Penthouse (1995)
67 One of Us Cannot Be Wrong – Leonard Cohen – Songs of Leonard Cohen (1968)
66 Hope – Arlo Parks – Collapsed in Sunbeams (2021)
65 I Don’t Believe in Anything at All – Cruel, Cruel Moon – Still Life (1996)
64 Glass Onion – The Beatles – The Beatles (1968)
63 Requiem – Richard Harris – My Boy (1971)
62 Can’t Get It Out of My Head – Electric Light Orchestra – Eldorado (1974)
61 A Wedding in Cherokee County – Randy Newman – Good Old Boys (1974)
60 Half a Person – The Smiths – single B-side (1987)
59 Holland Tunnel – John Phillips – John, The Wolf King of L.A. (1970)
58 Misty Mountain Hop – Led Zeppelin – Led Zeppelin IV (1971)
57 Rose Darling – Steely Dan – Katy Lied (1975)
56 It’s All Over Now, Baby Blue – Marianne Faithfull – Rich Kid Blues (1985)
55 To Love Somebody – Bee Gees – Bee Gees’ 1st (1967)
54 Ivory Coast – Destroyer – Ken (2017)
53 Satellite of Love – Lou Reed – Transformer (1972)
52 Uncle Bob’s Corner – Michael Hurley – Hi Fi Snock Uptown (1972)
51 My Cherie Amour – Stevie Wonder – single (1969)
50 (I’m) Stranded – The Saints – single (1976)
49 Gratitude Walks – American Music Club – Mercury (1993)
48 Johnsburg, Illinois – Tom Waits – Swordfishtrombones (1983)
47 Pretty (Ugly Before) – Elliott Smith – From a Basement on the Hill (2004)
46 Never My Love – The Association – Insight Out (1967)
45 Source Decay – The Mountain Goats – All Hail West Texas (2002)
44 Spill the Wine – Eric Burdon and War – single (1970)
43 (Pa) Ubu Dance Party – Pere Ubu – Dub Housing (1978)
42 Temporarily Out of Order – Skeeter Davis & NRBQ – She Sings, They Play (1985)
41 We Can’t Help You – Stephen Malkmus and the Jicks – Real Emotional Trash (2008)
40 Gravity of the Situation – Vic Chesnutt – Is the Actor Happy? (1995)
39 Visions of Johanna – Bob Dylan – Blonde on Blonde (1966)
38 Chain of Fools – Aretha Franklin – single (1967)
37 Wichita Lineman – Glen Campbell – Wichita Lineman (1968)
36 Diamond Dogs – David Bowie – Diamond Dogs (1974)
35 Bennie and the Jets – Elton John – Goodbye Yellow Brick Road (1973)
34 I Won’t Last a Day Without You – The Carpenters – A Song for You (1972)
33 Ode to the Exhausted – The Places – The Autopilot Knows You Best (2000)
32 Sara Smile – Hall & Oates – Daryl Hall & John Oates (1975)
31 Colors and the Kids – Cat Power – Moon Pix (1998)
30 The Lady Wants to Know – Michael Franks – Sleeping Gypsy (1977)
29 One Hundred Years from Now – The Byrds – Sweetheart of the Rodeo (1968)
28 Bessie Smith – Bob Dylan and the Band – The Basement Tapes (1975)
27 Take It or Leave It – Keith Stewart Band – Epic Hits (2001)
26 Stoney End – Laura Nyro – More Than a New Discovery (1967)
25 He Stopped Loving Her Today – George Jones – I Am What I Am (1980)
24 She Ain’t Right for You – Macy Gray – The Trouble with Being Myself (2003)
23 Angel from Montgomery – John Prine – John Prine (1971)
22 Sunny – Bobby Hebb – single (1966)
21 To Sir with Love – Lou Miami and the Kozmetix – single B-side (1982)
20 Serpent at the Gates of Wisdom – Robyn Hitchcock and the Egyptians – Respect (1993)
19 Tumbling Dice – The Rolling Stones – Exile on Main St. (1972)
18 Big Louise – Scott Walker – Scott 3 (1969)
17 It Makes No Difference – The Band – Northern Lights - Southern Cross (1975)
16 Black Cow – Steely Dan – Aja (1977)
15 MacArthur Park – Richard Harris – A Tramp Shining (1968)
14 Somebody Groovy – The Mamas & The Papas – If You Can Believe Your Eyes and Ears (1966)
13 Dizzy – Tommy Roe – single (1968)
12 I’ve Got to Have You – Sammi Smith – Something Old, Something New, Something Blue (1972)
11 In Dreams – Roy Orbison – In Dreams (1963)
10 Mariners Apartment Complex – Lana Del Rey – Norman Fucking Rockwell! (2019)
9 Cupid – Otis Redding – Remember Me (1992)
8 Some Velvet Morning – Nancy Sinatra and Lee Hazlewood – Nancy & Lee (1968)
7 Goodmorning Boyfriend – Tulip Sweet and Her Trail of Tears – Cry (2002)
6 Dancing Queen – ABBA – Arrival (1976)
5 Slow Education – Silver Jews – Bright Flight (2001)
4 Agitated – Electric Eels – single (1978)
3 Be My Baby – The Ronettes – single (1963)
2 Cupid Come – My Bloody Valentine – Isn’t Anything (1988)
1 Oh Bondage Up Yours! – X-Ray Spex – single (1977)