The Sopranos is known, of course, for its dynamite cast and its innovative story-telling, but the show (which can be streamed on HBO Now) also had a pretty impressive roster of guest stars who would lend their talents to just a few scattered scenes across no more than an episode or two. Like powdered sugar on a cannoli, these actors are an oft-forgotten but vital part of the show’s revered legacy, so we thought we’d celebrate the best.
J.D. Williams – Special K
Three years before he’d play the role of Barksdale corner man Bodie on The Wire, J.D. Williams made a brief appearance in the second episode of the first season of The Sopranos. It’s more than a blink-and-you-miss-it cameo, though. Williams’ moment of carelessness ends up setting off a series of events that impacts Christopher and Brendan rather severely.
Bookeem Woodbine – Massive Genius
After a night out in the city, Christopher and Adriana cross paths with rap mogul Massive Genius. While they become enamored with his extravagant lifestyle, he takes an interest in the internal workings of the Soprano family, both personal and professional.
Paul Mazursky – Sunshine
The five-time Oscar nominee first appeared as the dealer, Sunshine, for The Executive Game, a high-stakes card game that he “inherits” from his Uncle Junior in season two’s “The Happy Wanderer.” He shows up again in season three’s riveting “Amour Fou,” during a botched robbery attempt.
Frank Sinatra Jr. – Himself
A regular player at The Executive game, he shows his long-standing rapport with Tony’s crew, reassuring fish-out-of-water David Scatino (Robert Patrick in a season-long recurring role), that Paulie is “not just a nasty f*ck, he’s an incredibly nasty f*ck.” Paulie brushes off the ribbing, referring to Sinatra as “Chairboy of the Board.”
Sully Boyar – Dr. Krakower
After attending therapy sessions with Dr. Melfi, with and without Tony present, Carmela visits a contemporary of hers, Dr. Krakower, who wastes no time telling her under no uncertainty to leave her husband, and that he wouldn’t take payment from her, as he was unwilling to accept “blood money.” As Carmela pleads with him that “he’s a good man, basically,” Krakower snaps back, “you just told me he’s a depressed criminal.” It would end up being Boyar’s final role, as he died of a heart attack just two weeks before the episode aired.
Sam McMurray – Dr. John Kennedy
Junior’s reverence toward his surgeon, Dr. Kennedy, is shaken when he begins avoiding his phone calls after he seeks a second opinion on his stomach cancer. After Tony and Furio make it a point to show him the error of his disrespectful ways, I always liked to imagine this terrified Kennedy so much he enters the Witness Protection Program, assumes a new identity after being relocated to New Mexico before treating Walter White. That or Sam McMurray is just one of the most ubiquitous “that guy” actors out there.
Burt Young – Bobby ‘Bacala’ Baccalieri, Sr.
After having moved to Miami, Bacala’s cancer-stricken father comes back to Jersey to visit his grandkids. Taking advantage of him being back in New Jersey, Tony offers Bacala Sr. a chance to come out of retirement and help take care of a difficult situation. Being that it’s The Sopranos, there are dire consequences as a result.
Charles S. Dutton – Officer Wilmore
Possibly the only traffic cop in all of New Jersey with the gumption to give Tony Soprano a ticket, Officer Wilmore finds his world turned upside down when Tony takes advantage of his local government connections to squeeze him out of his job.
Lady Gaga – A.J.’s classmate
One night, after A.J. and his friends break into the school, things quickly escalate and school records, desks, and trophies all end up underwater. Cheering on the destruction? Lady Gaga in an uncredited appearance as “Girl by the pool #2.”
Isaach De Bankole´ – Father Obosi
Seeking to make a confession, Carmela reveals to the priest that she believes God is punishing her for Tony’s crimes. Obosi, a soft-spoken, thoughtful man of God gives her solace, telling her that God loves her more than she knows, and even speaks to the complexity of the world they live in, enabling her a whole new way to rationalize her living with her husband’s crimes.
Michael K Williams – Ray Ray
Looking for a place to hide out after a botched robbery attempt, Jackie Jr. gets taken in by Ray Ray at a housing project in Boonton. In a clever bit of foreshadowing, as his daughter teaches Jackie Jr. to play chess, Ray Ray looks at the game board at one point telling him bluntly, “Yo, man, I think you done for.”
Fairuza Balk – FBI Agent
Originally cast as FBI Agent Deborah Ciccerone for the season three finale “Army of One,” Balk opted not to return to the role once her character was expanded in the following season, and was recast with Lola Glaudini, who re-shot all of Balk’s scenes for all subsequent DVD and VOD releases.
Tobin Bell – Major Zwingli
Once he’s expelled from high school after cheating on a test, Tony and Carmela look into putting A.J. into military school, which Tony sees as a way of saving him from himself. Bell, best known as Jigsaw from the Saw franchise, gets a pretty good amount of range in the four minutes of screen time he gets as the major of a prestigious military academy. When Carmela explains she doesn’t approve of the school’s approach, his blunt response that “the mothers seldom do” is sublime.
Will Arnett – Agent Mike Waldrup
The husband of Agent Danielle Ciccerone (after she was recast), Arnett appears briefly in a couple of scenes, most notably commenting on how their infant child takes a liking to her big hair, an undercover tactic she’s using to get close to Adriana. It was one of his last dramatic roles, as he was cast as Gob Bluth on Arrested Development two years later.
Paul Dano – Patrick Whalen
A.J.’s pop-culture obsessed friend, Patrick, begins to push him for details into the seedy world that he imagines his father’s life to be.
Bruce Altman – Alan Sapinsly
A wealthy, WASP-y New Englander who enters into business with Tony when he becomes the favored buyer for his shoreside property, Whitecaps. Once circumstances change and Tony tries to back out, though, Alan refuses to pay him back his deposit, insisting it’s his right to withhold it. This leads to a special kind of torment courtesy of Tony, one that involves an old Dean Martin CD played at high volume.
Annette Bening – Herself
One of the show’s high-concept episodes, the majority of the storyline takes place in one of Tony’s dreams, including this bizarre scene where they’re introduced to Meadow’s boyfriend’s parents. The catch: His father is John Heard, who played the gambling addicted cop Vin Makazien in the show’s first season, and his mother is Annette Bening, who Tony recognizes, before she later references a scene from The Godfather.
David Lee Roth – Himself
Another celebrity at a Sopranos family poker game, Roth reminisces fondly of the tax-paying advantages of his rock star life. Namely, how he “used to be able to write off condoms.”
Hal Holbrook – John Schwinn
A former scientist portrayed by Emmy and Tony-winning actor Holbrook, Schwinn begins to discuss the oneness of life through quantum theory while watching a prize fight with Tony in rapper Da Lux’s hospital room.
Daniel Baldwin – Himself
Christopher’s dream project, the low-budget mob/horror movie “Cleaver” finally gets its premiere. After a failed attempt to cast Ben Kingsley, they manage to sign Daniel Baldwin, who ends up starring as the philandering mob boss who was very clearly modeled after Tony.
Sydney Pollack – Warren Feldman
Another Hollywood heavy-hitter who’d lend his talent to the show’s roster, Pollack played a surgeon who committed a series of brutal murders after catching his wife cheating on him. Now reduced to the role of custodian within the prison hospital, he becomes fast friends with Johnny Sack, who’s there himself due to his rapidly advancing cancer.
Nancy Sinatra – Herself
Keeping with his old-school style, Phil Leotardo hires Nancy Sinatra to sing at his party to celebrate him becoming the boss of one of New York’s five families. While many of the show’s characters are there to celebrate along side him, his position at the top sets events in motion that lead to the shows climactic final episodes.
