Written by Leslie Rosa

I grew up on Paul Simon’s music. My parents, like many of their generation, were attracted to the complex, nuanced, and poetic qualities of his songs in the 70s and 80s. It was only natural that his albums were played on our family’s record player and accompanied us on family road trips in cassette form or as a family sing-along. Even as I grew into a teen and then adult, however, Paul Simon was still there as the soundtrack, accompanying me as I studied the guitar, staying with me throughout college and helping me through some of the more vulnerable moments of my life.

Maybe the fact that he was a Queens kid like me had something to do with it: his childhood home was only minutes away from mine and we attended the same public junior high school—decades apart, of course.

This spring, my sisters, mother and I all met up in New York to see a show on his latest (final?) tour called A Quiet Celebration. It was night and day from when I saw him in the early 2000s at the Brooklyn Academy of Music, where the sound was explosive and the audience was dancing in the aisles. Due to hearing loss and aging vocal cords, Paul revisited his oeuvre in a way that made the material all the more expressive and heartfelt. That, in my opinion, is a true creative feat.

While absorbing the show, I was reminded what a wide range of emotional and sonic flavors he brings to his music: from the introspective hush of Hearts and Bones to the vibrant South African rhythms of Graceland, from the political protest of The Paul Simon Songbook to contemplations of the divine in Seven Psalms. And I thought: how fun would it be to pair each of his albums with an Italian wine? Italian wine, after all, shares an equally vast diversity albeit in aromas, flavors, sensations and history.

The first of two parts of an imaginative and, of course, very subjective, guide that pairs Paul Simon’s solo studio albums from 1965 - 1986 with a grape variety or wine that complements each one’s vibe. Hope you enjoy!

The Paul Simon Songbook (1965)

Cesanese

Before the full bloom of Simon & Garfunkel, there was The Paul Simon Songbook—raw, politically conscious, and introspective. Recorded in London, it’s filled with stark acoustic arrangements and lyrical poignancy.

Wine pairing: Cesanese is an ancient red grape from Lazio, near Rome—underrated, earthy, and surprisingly elegant when handled right. It’s a wine that rewards quiet attention and reveals emotional depth beneath a rustic exterior. That makes it a perfect partner for this stripped-down, early collection of some of Simon’s most enduring songs in embryonic form (“I Am a Rock,” “Kathy’s Song,” “Leaves That Are Green”).

Paul Simon (1972)

Dolcetto

Paul’s first post-Garfunkel solo album is introspective and emotionally transparent. Songs like “Mother and Child Reunion” and “Duncan” show an artist feeling out his solo voice, mixing folk, reggae, and gospel influences.

Wine Pairing

Dolcetto (meaning “little sweet one”) offers a juicy, accessible profile—plum, black cherry, and violets—yet is often dry, with a touch of bitterness on the finish. Much like this album, Dolcetto is underestimated; it’s playful yet layered, structured yet unconcerned with showmanship.

There Goes Rhymin’ Simon (1973)

Frappato

This album sees Paul hitting a more confident stride, with radiant hits like “Kodachrome” and “Love Me Like a Rock.” It’s bright, richly produced, and layered, with gospel choirs, Dixieland jazz, and string arrangements—but anchored by tender and moving lyrical moments.

Wine Pairing

Frappato. This Sicilian red is bright and aromatic, with red fruit, herbs, and a touch of spice. Frappato has bounce and charm, but carries enough earth and complexity to ground its vibrant personality—mirroring the album’s exuberant arrangements and thoughtful lyricism.

Still Crazy After All These Years (1975)

REFOSCO

Mellow, melancholic, and lush. This album won the Grammy for Album of the Year and includes reflective tracks like “50 Ways to Leave Your Lover.” It’s the sound of midlife nostalgic musings wrapped in grace.

Wine Pairing

From Friuli-Venezia Giulia, Refosco is a wine of shadows and structure—dark berries, herbs, iron, and a slight bitterness that cuts through any sweetness. It’s emotionally aligned with Still Crazy: smooth on the surface, complex beneath, and always edged with reflection.

One-Trick Pony (1980)

Susumaniello

This soundtrack album, tied to Simon’s film of the same name, features live performances and explores the life of a working musician. There’s groove here (“Late in the Evening”), but also weariness and resignation (“Long, Long Day”). It’s a record that doesn’t beg for attention — it earns it over time, through craft and candor.

Wine Pairing

Hailing from Puglia, Susumaniello (whose name means a “heavily-loaded donkey”, referring to the grape’s high yield) was long dismissed as a blending grape before being rediscovered in recent decades for its solo potential. Susumaniello offers ripe blackberry, earthy spice, and a touch of wildness. It’s soulful, a little rustic, and full of quiet conviction — a wine that tells its story with texture, not flash. Definitely not a one-trick pony (donkey?) just like this album.

Hearts and Bones (1983)

MONICA

Often overlooked, Hearts and Bones is perhaps Simon’s most personal and quietly devastating album. Written during and after his relationship with Carrie Fisher, it’s full of reflection, vulnerability, and lyrical precision. It also has one of my favorite Paul Simon songs of all time: “Rene and Georgette Magritte with Their Dog After the War”.

Wine Pairing

Monica, a Sardinian varietal, is soft and supple with notes of red fruit and herbs. It’s not flashy, but its gentle complexity and island-born resilience mirror the confessional tone and emotional richness of Hearts and Bones.

Graceland (1986)

Falanghina

A global smash and cultural milestone, Graceland fused American songwriting with South African rhythms. Joyful, political, and rhythmic, it reshaped world music in the Western pop sphere.

Wine Pairing

Bright, exotic, and full of vibrant energy, Falanghina’s citrusy, floral personality is the ideal pairing for Graceland’s South African rhythms and joyful spirit. A wine that feels like sunlight on skin.