25. Sam Stone John Prine (1972)
A grim song about a strung-out former soldier that remains a favourite of audiences who prefer their Vietnam vets to be total losers.
24. My Immortal Evanescence (2002)
A whimpering post-breakup tune in which lead singer Amy Lee pitifully mourns the end of a relationship over a piano accompaniment that sounds like Pachelbel after the Prozac wore off.
23. You don't bring me flowers Neil Diamond & Barbra Streisand (1978)
Neil and Babs phoned in this turgid song with all the energy of a ping-pong match played in zero gravity.
22. The River Bruce Springsteen (1980)
The title cut from Springsteen's fifth album, The River is the blue-collar hero's 473rd song about how bad blue-collar life is, featuring yet another unemployed dope from New Jersey hitched to an unhappy girl named Mary (every girl in Springsteen's songs is called Mary).
21. Tell Laura I love her Ray Peterson (1960)
Tell Laura was the first of the infamous teenage car-crash songs of the early 1960s, where adolescents get incinerated in fiery auto wrecks due to their altruism and stunning lack of common sense.
20. All By Myself Celine Dion (1996)
The Canadian superstar's bombastic cover of Eric Carmen's 1970s hit about loneliness is the audio equivalent of the fire-bombing of Dresden.
19. Woman's Prison Loretta Lynn (2004)
Despite her extensive catalogue of tears-in-your-beer country songs, the legendary Loretta Lynn outdoes herself with this mind-blowing murder tune which puts her on death row for blowing away her cheatin' husband.
18. Prayers for Rain The Cure (1989)
The following are some of the words found in the lyrics to Prayers for Rain: shatter, dull, kill, stifle, infectious, hopelessness, rain, suffocate, dirt, nowhere, desolate, drab, killing, fracture, stale, strangle, entangle, deteriorate, drearily, tired.
17. The Freshmen The Verve Pipe (1997)
Not to be confused with the Verve, the American faux grunge band the Verve Pipe hit no 1 in the US with this tragic number about two young men dealing with the suicide of a girl they both dated and later dumped.
16. The Rose Bette Midler (1980)
The Divine Miss M's biggest and most manipulative hit was first heard over the final scene in the movie The Rose where Midler's rock-star character drops dead in front of a live audience.
15. Maggie's Dream Don Williams (1984)
Nashville may have a rich heritage of depressing music but this hemlock-gulping country weeper will force listeners to throw themselves into a vat of possum poo.
14. Comfortably Numb Pink Floyd (1979)
This classic rock dirge appears on Pink Floyd's notorious magnum opus The Wall, the one album you can never listen to in its entirety unless you own a bong the size of a mop.
13. Brick Ben Folds Five (1997)
(NB: Many listeners, including me, first assumed Brick was about a relationship ending. We discovered later that it's about a couple getting an abortion.
12. Ruby, Don't take your love to town Kenny Rogers and the First Edition (1969)
Upbeat music does nothing to obscure the creepiness of this early Kenny Rogers song. Ruby is about a paralysed man who sits at home every night while his trampy wife Ruby dolls herself up before heading out to pick up any Billy Bob, Wyatt, or Bubba she can find.
11. One Metallica (1988)
The heavy metal band raised the depression bar dramatically when it based its gruesome song One on the world's most depressing novel, Dalton Trumbo's Johnny Got His Gun; it makes Foxe's Book of Martyrs read like Helen Fielding.
10. People Who Died The Jim Carroll Band (1980)
While most punk music sounds like screaming winos crammed inside a runaway shopping cart, this violent death anthem goes way beyond the usual mohawk bellowings.
9. Sister Morphine Marianne Faithfull (1979)
Though not as well known as the Rolling Stones' earlier version she helped write, Marianne Faithfull's 1979 cover version of the morbid Sister Morphine is infinitely more debilitating, if only because of the craggy quality of her voice.
8. Hurt Nine Inch Nails (1994)
Marvellously covered in 2002 by Johnny Cash, the original version of Hurt closes out Nine Inch Nails's The Downward Spiral, the perfect album to crank while you're tossing live hamsters into a blender.
7. Strange Fruit Billie Holiday (1939)
Strange indeed and insufferable, too. This notorious anti-lynching song unfortunately helped cement Billie Holiday's reputation as a wounded torch singer, gardenia optional.
6. DOA Bloodrock (1971)
An ode to the ephemeral joy that comes from being a corpse who perished in a plane crash, the sick DOA describes the searing pain in the victim's body, his blood oozing out of him while his mangled girlfriend lies nearby.
5. Seasons in the Sun Terry Jacks (1974)
This mawkish translation of the Jacques Brel song Le Moribond hit no 1 and tormented a generation of radio listeners with its mortal sappiness and earworm chorus ("we had joy, we had fun ... ").