Billy Joel B-SIDES

Billy Joel B-SIDES (S6 | E277)

Long before I was spinning records as Lester the Nightfly, I was a kid in Farmington Hills, Michigan obsessed with the tactile magic of a 45 rpm single. I remember the weight of it in my hands—the Billy Joel “Big Shot” 7-inch. While the A-side was the anthem of every 1970s disco-era hangover, it was the B-side, the frantic and virtuosic “Root Beer Rag,” that really stayed with my sisters and I. In fact Heidi became a huge Billy Joel fan. That single is the visual inspiration for this episode. Today, we’re stepping away from the overplayed radio staples to explore the sophisticated, gritty, and deeply musical corners of Billy Joel’s catalog. These are the tracks that define his range as a composer and storyteller.

We start with “Rosalinda’s Eyes” from 52nd Street. This track is a masterclass in Latin-infused jazz-pop, a tribute to Billy’s mother, Rosalind. With its breezy flute solo and bossa nova rhythm, it’s a far cry from the rock-and-roll bravado usually associated with him. It captures a specific New York romanticism—dreaming of a better life while working a gig in a Havana-style club. It’s followed by the raw, sprawling epic “Captain Jack.” While it’s one of his most famous early works, its length and bleak subject matter—addressing the suburban malaise and drug culture of the early ’70s—keep it off the “easy listening” playlists. It’s a powerful, uncomfortable, and essential piece of his history.

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The energy shifts with the iconic pairing of “Prelude / Angry Young Man.” The “Prelude” is a percussive piano workout that tests the limits of human dexterity, leading perfectly into the cynical, fast-paced observation of a man who believes his own hype. Then, we cool things down with “Half a Mile Away,” a soulful, horn-heavy track that feels like a lost Otis Redding session. It’s one of those tracks where Joel leans into his R&B influences, creating a song that feels like a Saturday night in the city when you’re just trying to outrun your responsibilities.

Next, we revisit the early days with “Everybody Loves You Now” from Cold Spring Harbor. It’s a biting, cynical track directed at someone whose ego has outgrown their surroundings. Despite its upbeat tempo, there’s a sharp edge to the lyrics that shows Joel was a formidable songwriter right out of the gate. We then move into the psychedelic, Beatles-esque production of “Laura” from The Nylon Curtain. It’s a heavy, neurotic track about a toxic relationship, featuring some of Joel’s most complex vocal harmonies and a dark, brooding atmosphere that contrasts beautifully with his more polished 80s work.

A LOVE FOR THE 45

No deep-dive into Billy Joel is complete without the aggression of “Stiletto.” Driven by a menacing bassline and Liberty DeVitto’s legendary drumming, it’s a song about the dangerous attraction of a femme fatale. It’s sharp, sophisticated, and sounds like a noir film set in Manhattan. We follow that with the emotional weight of “Summer, Highland Falls.” Many fans (and the man himself) consider this one of his finest compositions. It’s a philosophical look at the “sublimination of the soul,” balancing the “sadness and the euphoria” of life over a stunningly complex piano arrangement.

Track Name	Album Name	Artist Name(s)	Release Date	Record Label
Rosalinda’s Eyes	52nd Street	Billy Joel	10/13/78	Columbia
Captain Jack	Piano Man (Legacy Edition)	Billy Joel	11/7/73	Columbia/Legacy
Prelude / Angry Young Man	Turnstiles	Billy Joel	5/19/76	Columbia
Half a Mile Away	52nd Street	Billy Joel	10/13/78	Columbia
Everybody Loves You Now	Cold Spring Harbor	Billy Joel	11/1/71	Columbia
Laura	The Nylon Curtain	Billy Joel	6/23/82	Columbia
Stiletto	52nd Street	Billy Joel	10/13/78	Columbia
Summer, Highland Falls	Turnstiles	Billy Joel	5/19/76	Columbia
Sleeping With the Television On	Glass Houses	Billy Joel	3/12/80	Columbia
Big Man on Mulberry Street	The Bridge	Billy Joel	7/28/86	Columbia
I’ve Loved These Days	Turnstiles	Billy Joel	5/19/76	Columbia
Big Shot	52nd Street	Billy Joel	10/13/78	Columbia
Root Beer Rag	Streetlife Serenade	Billy Joel	10/11/74	Legacy/CBS/Sony
Where’s the Orchestra?	The Nylon Curtain	Billy Joel	6/23/82	Columbia

As we move into the 80s, we find “Sleeping With the Television On” from Glass Houses. This is a perfect piece of power-pop that captures the anxiety of the dating scene in the age of broadcast static. It’s lean, catchy, and incredibly relatable. Then comes “Big Man on Mulberry Street,” a theatrical, big-band jazz number from The Bridge. This track showcases Billy’s ability to write for an orchestra, channeling a swaggering, cinematic version of New York that feels like a midnight stroll through Little Italy.

A New Yorker Through and Through

We return to the reflective side of things with “I’ve Loved These Days.” It’s a bittersweet anthem about living beyond one’s means and enjoying the decline of a decadent lifestyle. It’s cinematic and weary, a perfect lead-in to the song that started this journey for me: “Big Shot.” Even as a massive hit, its inclusion here serves as the anchor to its B-side companion, “Root Beer Rag.” Hearing that frantic, ragtime instrumental always takes me back to the 45 rpm player in my room—it’s pure, unadulterated musical joy and technical wizardry that reminds us that, at his core, Billy Joel is a world-class player.

We close the set with the hauntingly beautiful “Where’s the Orchestra?” from The Nylon Curtain. It’s a poignant metaphor for the disillusionment of adulthood—the feeling that the show you were promised isn’t quite the one you’re seeing. It’s a quiet, introspective ending to a journey through a legendary career. Thanks for joining me on this deep-cut expedition. Whether you’re a lifelong fan or just discovering these tracks, I hope they give you a new appreciation for the man from Oyster Bay. Until next time, I’m PJ Ewing, and this is Lester the Nightfly. Keep the music playing.