36 Elliott Smith
Either/Or
(Kill Rock Stars, 1997)

https://www.youtube.com/watch?v=hPD-a1FjUtU

Smith often drew on personal experiences for his songs – in particular, drug abuse, failed relationships and his own psychological state – but arguably his third record, Either/Or, is the most confessional of his albums. “Between The Bars” addresses the debilitating nature of addiction – “the potential you’ll be that you’ll never see” – while “Alameda” bristles with alienation and defensiveness: “Nobody broke your heart/You broke your own/’Cause you can’t/Finish what you start”. Meanwhile, Smith mines his discomfort with his own growing popularity on “Pictures Of Me”: “Saw you and me on the coin-op TV/Frozen in fear every time we appear”.

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37 Paul Westerberg
Suicaine Gratification
(Capitol, 1999)

Kicking off with an ode to mid-life depression (“Get up from a dream and look for rain/Take an amphetamine and a crushed rat’s brain”), the third solo album by The Replacements’ guiding light is an extended essay in anxiety, commercial failure and the after-effects of alcoholism. Partly recorded in his Minneapolis basement, the music and mood is stripped bare. “Self-Defence” contemplates suicide as an escape route, “Sunrise Always Listens” recalls a long dark night of the soul, while “Best Thing That Never Happened” sums up a lifetime of disappointments.

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38 Ryan Adams
Heartbreaker
(Bloodshot, 2000)

The demise of previous band Whiskeytown coincided with Adams’ break-up with girlfriend Amy Lombardi. As a result, he poured his hurt into a debut solo album littered with references to loneliness, despair and lost youth. Recorded in Nashville with Gillian Welch, David Rawlings and producer-instrumentalist Ethan Johns, Heartbreaker is a rich set of baleful country-folk songs made all the more compelling by Adams’ windblown delivery. Yearning Emmylou Harris duet “Oh My Sweet Carolina” was a highlight, though it doesn’t get much more affecting than “Come Pick Me Up”, a soulful paean to lost love, or “Call Me On Your Way Back Home”, on which he croons: “I just want to die without you”.

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39 Rodney Crowell
The Houston Kid
(Sugar Hill Records, 2001)

Arguably better known to wider audiences through his association with others (long-serving sideman to Emmylou Harris, husband of Johnny Cash’s daughter, Rosanne), The Houston Kid found Crowell telling his own story in a song cycle about growing up in the rough, low-rent east side of the city. “Telephone Road” is vividly descriptive in its portrait of his formative years, difficult circumstances continuing to make their presence felt in the saloon bar twang of “Rock Of My Soul”. The struggles of finding oneself inform “Why Don’t We Talk About It?”, while the bold rewrite of a Cash classic, “I Walk The Line (Revisited)” addresses the hoops he jumped through to impress his father-in-law.

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40 Beck
Sea Change
(Geffen, 2002)

https://www.youtube.com/watch?v=jFIVUpSpMJw

Three weeks before his 30th birthday, Beck found out that his girlfriend of nine years, Leigh Limon, had been cheating on him with a member of the LA band Wiskey Biscuit. Beck responded with a dozen pieces of wrecked resignation. “These days I barely get by,” he groans over a sympathetic slide guitar on “The Golden Age”, “I don’t even try.” Beck’s father, David Campbell, provides elegiac string arrangements throughout, but lyrics like “It’s only tears I’m crying/Only you I’m losing/Guess I’m doing fine”, scarcely need much help to tug at the heartstrings. Even Beck’s characteristic studio japery – like the backwards effects on “Lost Cause” – seem reflective of his inner turmoil.