Before pivoting to television in his 60s, Adler spent decades working behind the scenes on over 50 Broadway productions. But to millions of television fans, he will forever be remembered as Herman “Hesh” Rabkin, the sharp, wise, and pragmatic music executive who served as Tony Soprano’s most trusted advisor across all six seasons of HBO’s The Sopranos.
To celebrate his legacy, here are 5 essential Sopranos episodes that highlight Jerry Adler’s brilliant performance.
1. “A Hit Is a Hit” (Season 1, Episode 10)
This episode puts Hesh front and center as a former music mogul whose past comes back to haunt him when a rival rapper demands royalties for old Black artists Hesh produced in the 1960s. Adler delivers some of the series’ most iconic lines with deadpan perfection, famously schooling Christopher Moltisanti’s wannabe rock band with the timeless verdict: “A hit is a hit. And this, my friend, is not a hit.”
2. “Chasing It” (Season 6, Episode 16)
In one of Adler’s most poignant dramatic turns, a mounting $200,000 loan between Tony and Hesh threatens their decades-long friendship. As Tony’s gambling addiction sparks unsettling resentment toward his old friend, Adler portrays Hesh’s growing fear, quiet dignity, and profound heartbreak—compounded by the sudden loss of his partner, Renata—with devastating subtlety.
3. “The Sopranos” / Pilot (Season 1, Episode 1)
Introduced in the show’s very first hour, Hesh is established as the elder statesman and voice of reason in Tony’s orbit. Adler immediately sets the tone for the character, counseling Tony on an HMO scam at Satriale’s while offering seasoned, unflappable wisdom that made him an indispensable sounding board throughout the series.
4. “The Happy Wanderer” (Season 2, Episode 6)
Set against the backdrop of the high-stakes “Executive Game” poker match, Hesh brings veteran calm to a room full of volatile mobsters. Adler shines as he trades sharp banter with Tony while warning younger mobsters about the dangerous psychological traps of unchecked debt.
5. “Remember When” (Season 6, Episode 15)
As Tony and Paulie head off to Miami to lay low, Hesh remains a steady anchor back home in New Jersey. The episode highlights Hesh’s unique position as one of the few surviving figures from the old guard who can speak candidly about the past without falling prey to foolish nostalgia.
Adler’s ability to imbue Hesh with warmth, tactical shrewdness, and dry humor turned a supporting character into one of cable television’s most memorable figures.
