Believe it or not, I’ve been publishing music reviews for more than 20 years now, and since the very beginning I’ve had a habit of celebrating my birthday with a round-up of all-time favorites— some years a simple top 10, sometimes an indulgent top 100. It’s really just an excuse to spend some time meditating on the music that’s been most formative for me, and this year I thought I’d split the difference with a top 50— generous but (hopefully) not ridiculous.
I compiled this list mostly by pure instinct: These are more or less the first 50 albums that came to mind, with just a few records swapped-out and re-ordered upon further reflection. As with any such list, there are significant omissions: For example, this top 50 underplays the role of hip-hop in my life, and completely glosses over my enthusiasm for Brazilian music, Delta blues, and salsa. Hardcore punk is just barely represented, and classic country not at all (unless you count a Rosanne Cash album from the 1980s as classic country, which, come to think of it, you should). And of course, there are major artists whose albums just barely missed the cut: I can’t believe I listed my top 50 albums of all time without any mention of Joni Mitchell, Willie Nelson, Waylon Jennings, Louis Armstrong, The Roots, Outkast, De La Soul, R.E.M., U2, or Taylor Swift!
But even with these notable gaps, I think this is a pretty compelling synopsis of my tastes. So without further preamble… here are the 50 albums I’d hate to be without.
50) The White Stripes - Get Behind Me Satan (2005)
Even on their weirdest, most guitar-less album, The White Stripes still sound like The White Stripes: Jack howls about birds and bees, lust and betrayal, and his pianos and marimbas thump almost as hard as Meg’s drums.
49) Yo La Tengo - Fakebook (1990)
On their first all-covers album, the venerable indie rock band revels in the enigmatic, the inscrutable, the eccentric, and the obscure— all of it played with earnest affection. This album perfectly captures the joy in having niche interests, secret obsessions that you share with just a few.
48) Turnstile - Time & Space (2018)
I’m a latecomer to hardcore, and like most recent converts, my entry point was Turnstile. On this album, they engineer a perfectly-paced 25 minutes of slamming riffs, relentless grooves, bursts of melody, and spacey palette-cleansers.
47) Rhiannon Giddens with Francesco Turrisi - There is No Other (2019)
A celebration of acoustic instruments, folk traditions, and song as a connective tissue that bridges cultures and geographies. Giddens’ opera training is evident throughout, with each song conveying power and precision in equal measure.
46) The Beatles - Sgt. Pepper’s Lonely Hearts Club Band (1967)
Every band borrows from The Beatles, but none have ever matched their flare for whimsy, something that’s abundantly clear on this extended exercise in dress-up and make-believe. The band’s instinctive affection for British tradition adds a melancholy subtext to their psychedelic innovations.
45) Kris Davis - Diatom Ribbons (2019)
The album I’m most likely to reach for when I want to flirt with the jazz avant garde. Individual moments pivot from melody to groove to chaos, but there’s incredible beauty and care in Davis’ overarching design.
44) Kate Bush - Hounds of Love (1985)
Much of the best pop music emanates carnality, but Kate Bush has always seemed more obsessed with the subconscious. Her masterpiece excavates deep-seated dreams and desires, acting them out across a series of synth innovations that are simultaneously strange and accessible.
43) Paul and Linda McCartney - Ram (1971)
On this appealingly rowdy, homespun delight, Paul extols the quiet life, takes veiled shots at John, and indulges in a little good old-fashioned nonsense. The DIY ethos has seldom sounded so carefree and joyous.
42) The Beach Boys - Pet Sounds (1966)
The closest thing to classical music you’ll find on this list— an album that takes teenage angst and young-adult existentialism seriously, rendering them in painstakingly beauty and extravagant detail.
41) Alvvays - Blue Rev (2022)
An exhaustive taxonomy— dream-pop, power-pop, jangle-pop, shoegaze, you name it— condensed into one perfectly-paced, explosively tuneful record. Even the underground classics that influenced this album rarely reached this level of melodic glory, emotional acuity, or hooks-per-minute.
40) Tom Waits - Rain Dogs (1985)
Part musical theater and part surrealist comedy act, Rain Dogs ultimately creates a musical language all its own. Waits creates oversaturated renderings of seedy bars, questionable street corners, and smoke-filled cab rides, honoring his outcast characters by portraying them with humor and affection.
39) Charles Mingus - Mingus Mingus Mingus Mingus Mingus (1964)
Mingus’ boisterous, large-ensemble approach never sounded better than it did here, on a set of greatest hits revisited. Imagine the Duke Ellington Orchestra channeling the soulful swagger of Ray Charles and you have some idea of what this rowdy record sounds like.
38) Bob Dylan - John Wesley Harding (1967)
Following a couple of years of electric mayhem, John Wesley Harding marked Dylan’s return to acoustic music— but not to straightforwardly topical songwriting or familiar folk forms. Instead, he delivered this endlessly mystifying collection of riddles, parables, prophetic utterances, cryptic Old Testament allusions, and— on the final two songs— affectionate country-rock love songs.
37) D’Angelo - Voodoo (2000)
The deepest, gnarliest funk, slowed down and stretched out into an 80-minute odyssey of groove. Few albums create their own fluid sense of time the way this one does, and fewer still are as haunted by generations of soul, R&B, hip-hop, and African music, all converging into something timeless and original.
36) Brian Blade & The Fellowship Band - Season of Changes (2008)
Gets at just about everything I love about jazz: Earthiness, spiritual questing, ambition, accessibility, the combustible energy of skilled improvisers in perfect sync. I can’t think of a better example of music that starts with familiar forms (folk and gospel), but builds toward something stratospheric.
35) The Beatles - Abbey Road (1969)
I can’t help but be deeply moved by the subtext of this one: Though their union had fractured beyond repair, The Beatles were able to summon the old magic just one more time, sounding like an honest-to-goodness band, still capable of pairing bracing experiments with childlike whimsy, sophisticated suites, and love songs of unsurpassed beauty.
34) Bob Dylan - Time Out of Mind (1997)
Inspired by heartbreak and mortality, these songs employ the language of country-blues, yet they have just as much in common with ancient wisdom literature: In his anguish and despair Dylan often sounds like he’s living through Job or Ecclesiastes. His roadhouse blues are wrapped in a holy-moment glow, courtesy of suitably atmospheric production from Daniel Lanois.
33) Otis Redding - Otis Blue: Otis Redding Sings Soul (1965)
An incomparable demonstration of soul music virtuosity— in just half an hour’s time, Redding blazes through feel-good ballads, down-and-dirty blues, and gospel-tinged laments. It’s all held together by tight, in-the-pocket performances from the Stax house band, setting a high watermark for studio musicianship.
32) Gillian Welch - Time (The Revelator) (2001)
Invoking patron saints John Henry and Elvis Presley, Welch and her partner Dave Rawlings write a set of ruminative songs about every artist’s desire to do good work that will last, even as they reckon with the obliterative tides of time. They rely on little more than deep harmonies and guitar pyrotechnics to enliven songs born of hillbilly music, standards, and old-time rock and roll.
31) Duke Ellington - Money Jungle (1963)
While many of the best jazz records convey a sense of sympathetic connection between musicians, Money Jungle is a masterpiece of disharmony— fraught sessions boiling over into music marked by hard edges, tension, and aggression. There is considerable pleasure in hearing Duke— by this point an elder statesman, considered passé by some— push his younger sidemen to play harder, faster, and hipper.
30) Prince - Sign o’ the Times (1987)
A work of staggering musical ambition and startling moral clarity that sums up its era while still sounding timely today. Prince addresses rising consumerism, sexual confusion, and the fear of infectious disease with a series of club anthems, slow jams, exhortations to dance, and invitations to the Cross.
29) Rod Stewart - Every Picture Tells a Story (1971)
Years of middlebrow disco and rote Songbook revues have eroded Rod’s rock and roll credibility — but when he was good, he was the greatest. On his masterpiece, he makes contemporary folk songs sound like ancient wisdom, and rock-and-roll oldies sound like they were written just this morning. Well-curated covers gel into a loose bildungsroman, equal parts ribald and romantic.
28) Thelonious Monk - Thelonious Monk Trio (1954)
With due respect to all the great horn players he worked with, this feels like Monk in his purest distillation— bending his childlike whimsy to accommodate stride piano and barrelhouse blues, with extra firepower supplied by a couple of all-time great drummers.
27) Beastie Boys - Paul’s Boutique (1989)
I can’t overstate how much my aesthetic worldview has been shaped by the fearless pan-culturalism of the Beastie Boys— how they treat all of pop culture as their playground, upholding Dylan records and Hanna-Barbera cartoons as equally sacred texts. Their collective persona here is one of endearing adolescence: Sure, they think about boobs a lot, but they can still take a minute to remind us that racism is bad.
26) Duke Ellington - … and His Mother Called Him Bill (1968)
Following the death of boon collaborator Billy Strayhorn, Ellington was bereft. Rather than wallow in despair, he assembled his full orchestra for a recording session to honor Strayhorn’s genius as an arranger. The result is one of his most deeply-felt albums: A pristinely-recorded collection that sounds by turn disbelieving, joyful, raging, and broken-hearted.
25) Aretha Franklin - Spirit in the Dark (1970)
This is how I most want to hear Aretha: Sitting at the piano, backed by a sympathetic band, keeping a relaxed vibe as she rolls through a series of well-curated blues, soul, and gospel songs. She is a powerhouse talent, best-served by a low-key, casual setting.
24) A Tribe Called Quest - Midnight Marauders (1993)
Over their grittiest and funkiest beats, the jazz-rap pioneers conjure the spirit of hip-hop at its most boisterous, jocular, and carefree. The beats sound so crisp I could almost be persuaded there was a live band in the mix. And the bonhomie between Q-Tip and Phife Dawg was never more natural or compelling, cementing their stature as rap’s greatest double act.
23) Rosanne Cash - King’s Record Shop (1987)
Subsequent generations of country-singing women stand on the shoulders of Rosanne Cash, thanks to this record in particular— crisp and colorful, appreciative of tradition but unbeholden to it. You can credit producer Rodney Crowell with how great it sounds, but credit Cash for writing songs in which women have interiority, and are never content to be supporting characters in someone else’s life.
22) The Beatles - Rubber Soul (1965)
For all their technical and conceptual innovations, it can be hard to remember that The Beatles were an actual band, more than capable of filling a room with joyful ruckus. This is the album I reach for when I just want to hear them play together in seamless harmony.
21) Bob Dylan & The Band - The Basement Tapes (1975)
Documenting what’s arguably the most fruitful songwriting retreat of all time, The Basement Tapes finds Bob and his buddies chuckling and howling through a series of myths, legends, tall tales, bawdy jokes, and cheerful nonsense. Its loose spirit complements its rich balance of folklore and philosophizing.
20) Miles Davis - In a Silent Way (1969)
After years spent pushing boundaries, this is the album where Miles finally started deconstructing jazz altogether, landing somewhere closer to ambient music. Over the course of two beautiful and leisurely compositions, Miles and his band emanate mystique, their music rarely rising above the volume of a whisper.
19) Elvis Costello & Burt Bacharach - Painted from Memory (1998)
A seamlessly-constructed study in heartache, buffeted by pitch-perfect melodies, sly humor, and unashamedly emotional arrangements. When I need to sit with my feelings and to be enveloped in the warm glow of melancholy, this is the first album I reach for.
18) The Rolling Stones - Exile on Main St. (1972)
When I think of The Rolling Stones, I think of menace, decadence, and unrepentant sleaze. All of that’s present here, except for maybe the unrepentant part: This may be the only Stones album to meaningfully reach through the darkness toward light, redemption, and— in at least one song— the actual face of Jesus. It's also their most believably lived-in excursion into country, gospel, soul, and blues.
17) Sam Phillips - Martinis & Bikinis (1994)
For a brief moment in the 1980s, Phillips was one of Christian music’s most promising starlets; she pushed that aside, along with CCM’s pat moralism and right-wing drift, to make music that wrestles more honestly with faith and doubt. The T-Bone Burnett-produced Martinis & Bikinis is her punchiest work: Not just a work of incredible moral clarity, but one of the most colorful and convincing guitar-pop albums of the 90s.
16) Prince & The Revolution - Parade (1986)
For me, this is the fullest flourishing of Prince’s weird genius— an endlessly inventive concoction of rumbling, hard-edged funk with opulent, richly-textured psychedelia. The lyrics include cryptic religious imagery that’s endlessly fascinating, plus some of his best-ever jokes.
15) Joe Henry - Civilians (2007)
One of the most elegant and carefully-considered singer-songwriter albums of all time, weaving songs about wayward lovers with laments for a wayward nation. God is invoked in nearly every song, his watchfulness providing the album with real theological weight.
14) D’Angelo - Black Messiah (2014)
One of the only albums I can think of that was both long-gestated and rush-released. Its deep textures and lived-in funk suggest the culmination of 14 years’ careful craft, while its unyielding affirmations of human dignity speak to the raw urgency of its particular political moment.
13) Duke Ellington - The Popular Duke Ellington (1967)
Following decades spent on the road as America’s most venerated bandleader, Duke finally took advantage of the long-player format, getting his band together to play their greatest hits with warmth and familiarity. It sounds incredible, and bears witness to a composer uncommonly gifted in conjuring melody, whimsy, and romance.
12) The Beatles - Revolver (1966)
The text: A crisp, colorful, kinetic, and endlessly imaginative rock and roll album, establishing a still-unchallenged template for what modern pop can be. The subtext: The joy of innocence versus the darkness of adulthood, earnest whimsy versus arch cynicism, tradition versus transgression, and four men who are obviously drifting apart yet still sound like they can do anything together.
11) Bettye LaVette - The Scene of the Crime (2007)
A masterpiece of interpretive singing: Though nine out of 10 songs are covers, LaVette uses them to tell her story of being chewed up and spat out by the music industry, of years of disappointment and struggle, and of late-in-life triumph. As her backing band, the Drive-by Truckers are sympathetic, gritty, and smart enough to stay out of the way.
10) Miranda Lambert - The Weight of These Wings (2016)
An exemplary work of long-form country storytelling: Lambert uses the road as a controlling metaphor to explore her prodigal wanderings and her quest for a love more potent than her regrets. I love the played-up theatricality she brings to her hell-raising classics like Crazy Ex-Girlfriend, but am drawn even more to the nuanced intimacy she conjures here.
09) Peter Gabriel - So (1986)
Probably the weirdest album to ever become a #1 blockbuster, So revels in contradictions: State-of-the-art studio craft and indigenous musical traditions. Brazen carnality and unashamed spirituality. Quiet meditations and strutting satires. I think of it as a series of dreams, sometimes cryptic but always emotionally resonant.
08) Erykah Badu - Mama’s Gun (2000)
Badu synthesizes the lessons learned from all her soul- and R&B-singing elders, drawing them together into a strikingly idiosyncratic album that never feels musty or overly referential. Through a perfectly-paced series of addicting grooves and warm live-band performances, she strikes a nimble balance between tough-talk and vulnerability. You get to the last song before realizing that it’s been a breakup album all along.
07) Miles Davis - Kind of Blue (1959)
Maybe the most predictable “desert island” pick on the entire list: This unpretentious masterpiece is the jazz album you own even if you don’t own any other jazz albums. To know Kind of Blue is to affirm that it’s endlessly likable, disarmingly modest, casually charming. It is the platonic ideal for small-group improvisation, every voice completely distinctive yet blending into a seamless whole.
06) Over the Rhine - Good Dog Bad Dog (1996)
These intimate home recording were born out of a season of writer’s block— but clearly the dam finally burst: These are endlessly articulate songs about coping with failure, navigating the compromises associated with the creative life, and learning to receive grace.
05) Ray Charles - The Birth of Soul (1991)
Collecting Charles’ early Atlantic sides, this is the only two-and-a-half-hour album that I regularly play from front to back. It sounds like a superhero origin story: Charles begins the album clutching loose threads from the gospel, jazz, and blues traditions, then quickly discovers that he can do anything he wants with them. It remains thrilling to hear the master inventor at work, cranking out one sensational single after another, leaving whole new musical worlds in his wake.
04) The Innocence Mission - Birds of My Neighborhood (1999)
In immaculate stanzas of devotional poetry, these quiet songs reflect on the struggle to keep the faith and hold on to joy even through seasons of disappointment— listen closely and you’ll hear references to barrenness, sorrow, and long-hoped-for children. This consoling, autumnal album has been a companion through spiritual droughts, global pandemics, and personal crises; it’s prefect for Lent, but because of its allusions to another Long Expected Child, I also play it every Advent.
03) Allen Toussaint - The Bright Mississippi (2009)
A dozen songs from or about New Orleans, played with palpable glee by one of the city’s most treasured piano-playing statesmen. His joie de vivre never compromises his smooth, suave style, and the small studio band gracefully follows his lead. I can’t think of another album that better exemplifies how standards can be vehicles for personal expression; nor another album that provides me so much uncomplicated joy.
02) Bob Dylan - Love & Theft (2001)
My favorite Dylan, not least because it’s the one with the best jokes, and because it’s the one where he sounds like he’s having the most fun. The songs — complicated, contradictory, strangely legible, assembled from old blues idioms and Groucho Marx routines— are like maps and legends for all the roads he’s traveled: The rural mystique of John Wesley Harding, the boisterous myth-making of The Basement Tapes, the careening energy of Highway 61 Revisited, and a few subtle reminders that his Born Again era was no joke at all.
01) Joe Henry - Tiny Voices (2003)
Among contemporary songwriters, Joe is unparalleled at writing songs that sound like they could be lost gems from the Great American Songbook. It is relatively easy to imagine, say, Tony Bennet singing these melodies, though comparatively hard to imagine him delivering the lyrics about God’s disruptive love and humanity’s preference for comfortable self-deception. It’s harder still to imagine any straight-laced song-and-dance man assembling this crack team of jazz and rock studio pros, whose tunefulness teeters tantalizingly close to chaos.