A Bittersweet Ode to Unrequited Longing
The song “You Could Drive a Person Crazy”, as performed by David Cassidy, Shaun Cassidy, and their brother Patrick Cassidy, is a tender, playful yet aching reminder of how love can toy with our hearts—intoxicating and maddening all at once.
When we think of David and Shaun Cassidy, we often remember them as pop idols of their era, beloved by generations of young fans. But in 1996, the two brothers came together for something much more intimate and musically refined: a live performance at the S.T.A.G.E. Benefit Concert (held March 8, 1996, at the Doolittle Theatre in Hollywood), captured on the album Sondheim: A Celebration.
On that occasion, David, Shaun, and their brother Patrick sang Stephen Sondheim’s classic from the musical Company, “You Could Drive a Person Crazy.” This was a rare trio moment — the Cassidy brothers blending their voices in harmony, gently teasing yet emotionally sincere.
Chart Performance & Release
Interestingly, “You Could Drive a Person Crazy” as recorded by the Cassidy brothers was not released as a single, and therefore doesn’t have a peak position on mainstream pop charts. Rather, it exists within the context of the S.T.A.G.E. benefit concert recording. The album itself, Sondheim: A Celebration, was released by Varèse Sarabande in 1996.
So while there’s no chart ranking for this particular trio version, its significance lies elsewhere — in its musical legacy, its emotional resonance, and the symbolism of three Cassidy brothers paying tribute to Sondheim’s genius.
The Story Behind the Song
To fully appreciate this performance, it helps to remember the broader story. The concert was a benefit event, highlighting Sondheim’s work, and the Cassidy brothers were invited not just as pop icons but as sincere musicians. According to David Cassidy’s own discography notes, the three of them did a “sendup” of “You Could Drive a Person Crazy” — suggesting a playful, affectionate take rather than a purely theatrical one.
David Cassidy later spoke about the event: during rehearsal, the brothers relaxed, teased each other, and infused the performance with their real-life brotherly bond. For fans who grew up watching David on television and Shaun in his teen idol days, hearing them join voices in this Sondheim piece was a profound, nostalgic moment — as if they were stepping into a more mature chapter of their musical journey.
The Meaning & Emotional Weight
Stephen Sondheim’s “You Could Drive a Person Crazy” is from Company (first produced in 1970), and it’s lyrically clever, full of wit, and emotionally layered. The song describes a character who is confusing, elusive, and charming — someone who teases the object of their affection, making them feel both wanted and frustrated. The humor is sharp, but underneath it is a real ache: the longing to be seen, to be fully understood, to be loved even when one drives the other “crazy.”
When sung by the Cassidy brothers, this song takes on an extra dimension. Their voices — trained in pop, in harmony, in sibling interplay — lend it a warmth that pulls at memory. For an older listener, someone who perhaps followed David and Shaun in the days of teen magazines and Saturday morning TV, this performance feels like a homecoming: the cultural icons have grown, matured, and yet they return to something deeply theatrical, deeply heartfelt.