David Chase‘s The Sopranos was a landmark series that marked a new era in television with its innovative writing, cinematic atmosphere, and memorable characters who were played by an array of talented stars, including James Gandolfini, Lorraine Bracco, Edie Falco, and Dominic Chianese. Like any great show, there are numerous reasons why The Sopranos was and continues to be one of the most talked-about series, but one element that stands out, without question, is its collection of notable guest stars.
Throughout the show’s six-season run, a slew of familiar faces, such as John Heard, Frankie Valli, and Robert Loggia, delivered memorable performances that not only elevated the show’s overall popularity but also maintained an intriguing quality of unpredictability. The show also featured one-time guest stars, including Hal Holbrook and Burt Young, who, despite their limited screen time, ended up stealing the entire episode, which is not an easy task, especially up against a force like Gandolfini. Out of all the big names who appeared in the show, these are the ten best guest stars from The Sopranos, ranked!
10
Polly Bergen as Fran Feldstein
“In Camelot” Season 5, Episode 7 (2004)
In Season 5, episode 7, Tony goes to visit his parents’ grave site and unexpectedly meets his father’s longtime goomah, Fran Feldstein, played by classic film star, Polly Bergen. Bergen starred in several classic movies, including Move Over, Darling, and Cape Fear, starring Gregory Peck and Robert Mitchum, and also had a moderately successful television career, appearing in hit shows such as Alfred Hitchcock Presents, The Love Boat, and Murder, She Wrote.
Bergen was originally recommended for the role of Feldstein by the show’s casting director, Georgianne Walken, who, after reading the script for the episode, immediately thought of the former Hollywood starlet. When Bergen was approached about the part, she was already a fan of the show and accepted the role without hesitation. Despite only appearing in one episode, Bergen’s performance as the obnoxious and self-serving Feldstein left a lasting impression on fans, especially her rendition of Happy Birthday, Mr. President, which is easily one of the most cringeworthy moments in the entire show.
9
Peter Bogdanovich as Dr. Elliot Kupferberg
“Toodle-F*cking-Oo” Season 2, Episode 3 (2000)
Fans first meet legendary filmmaker Peter Bogdanovich in “Toodle-F*cking-Oo,” as Dr. Jennifer Melfi’s (Lorraine Bracco) psychotherapist, Dr. Elliot Kupferberg, whose sessions with Melfi give fans a glimpse into her life outside her usual-professional setting. Bogdanovich was Orson Welles‘ protégé who started as an actor and film journalist before rising to prominence directing a string of monumental movies, including What’s Up, Doc?, The Last Picture Show, and the Oscar-winning road dramedy, Paper Moon.
Chase was a fan of Bogdanovich and his work, specifically his performance in the series Northern Exposure, in which he not only proved his acting chops but also impressed Chase. While Bogdanovich’s character served as a sounding board for Melfi’s issues with Tony, the majority of fans remember Dr. Kupferberg for always having a bulky gray water bottle on hand during his sessions. Ironically, the water bottle was originally Bogdanovich’s, and since no one had any qualms about it, it eventually became an unofficial prop for his character.
8
Tim Daly as J.T. Dolan
“In Camelot” Season 5, Episode 7 (2004)
Known for his role as Joe Hackett on the hit ’90s sitcom, Wings, Tim Daly made his first appearance in The Sopranos in Season 5’s “In Camelot” as a young screenwriter, J.T. Dolan, who meets Christopher Moltisanti (Michael Imperioli) while in rehab and makes the fatal mistake of connecting with him after treatment. While Dolan’s addiction issues make him an easy target, Chrissy is mainly drawn to Dolan for his success as a screenwriter and essentially sees him as his ticket into the industry without having to put in the hard work himself.
At first glance, Dolan may seem like a throwaway character, but in some sense, he represents the person and the life that Chrissy had always wanted for himself, exposing another emotional aspect of the misguided mobster. Daly appeared in a total of four episodes of The Sopranos, and in 2007, his performance earned him an Emmy Award nomination for Outstanding Guest Actor in a Drama Series, making the former Wings star one of the series’ best guest stars.
7
Burt Young as Bobby Bacala Sr.
“Another Toothpick” Season 3, Episode 4 (2001)
Burt Young makes a one-time appearance in “Another Toothpick” as Bobby Bacala’s (Steve Schirripa) terminally ill father, Bobby Sr., who, at Tony’s request, comes out of retirement to whack his godson. Young was a versatile actor who was best known for his role as Rocky Balboa’s brother-in-law, Paulie Pennino, in the Rocky films, which earned him an Oscar nomination for his performance in the first film. He also appeared in other hit movies from the 1970s and 1980s, such as Chinatown, Once Upon a Time in America, and The Pope of Greenwich Village.
There is much more to Young’s performance as Bacala Sr. than an intense showdown of gunfire and mayhem. Bacala Sr. represents the mindset and morality of the traditional old-school gangster, providing viewers with an insightful comparison between the past and present generations of mobsters, with his tragic but triumphant death symbolizing the end of an era in the American mafia. Young’s appearance in The Sopranos might be brief, but his performance as the wily and fearless Bacala Sr. sticks firmly in the back of fans’ minds as one of the show’s finest.
6
Hal Holbrook as John Schwinn
“The Fleshy Part of the Thigh” Season 6, Episode 4 (2006)
In “The Fleshy Part of the Thigh,” Tony spends his remaining days in the hospital with a physicist, John Schwinn, played by stage and film star Hal Holbrook. Holbrook originally gained notoriety for his one-man show, Mark Twain Tonight!, as the famous author, which earned him a Tony Award for Best Actor in a Play in 1966. Aside from his frequent performances as Twain, Holbrook appeared in an assortment of notable movies, including All the President’s Men, The Firm starring Tom Cruise, and Steven Spielberg’s Academy Award-winning film, Lincoln.
Holbrook’s appearance as Schwinn added gravitas to the show’s exploration of legacy and regret and essentially delivered a powerful and thought-provoking performance that steals the entire episode. The Oscar-nominated actor captivates viewers with his character’s philosophical outlook and sparks their curiosity with his words of wisdom and insight that only a talent of Holbrook’s caliber could achieve with such precision. Holbrook might not have been as big a star as some of the other guest stars on the show, but his performance as Schwinn lingers with viewers long after the credits have rolled, rightfully earning him a spot on the list.
5
Robert Loggia as Feech La Manna
“Two Tonys” Season 5, Episode 1 (2004)
Robert Loggia made his debut in Season 5’s “Two Tonys” as one of the show’s most volatile and memorable antagonists, Feech La Manna. With a career spanning over six decades, Loggia was a reputable film star who appeared in now-iconic classics such as Big, Brian De Palma‘s Scarface, and Jagged Edge, which earned him an Oscar nomination for Best Supporting Actor. Loggia also had a solid television career, appearing in popular shows including Magnum P.I., Charlie’s Angels, and The Rockford Files.
The actor’s reputation for playing tough guys and his esteemed career made him an obvious choice to play a straightforward hothead like Feech, who quickly becomes a never-ending headache for Tony. Unfortunately, Loggia was suffering from early-stage Alzheimer’s disease, which made it difficult for him to remember his lines and ultimately led to his character’s abrupt exit from the show. While it would have been great to see where Feech’s story was originally intended to go, Loggia didn’t disappoint with his powerhouse performance as the old-school mafioso who is, hands down, recognized as one of the most wicked characters in The Sopranos.
4
Frankie Valli as Rusty Millio
“All Happy Families…” Season 5, Episode 4 (2004)
There have been several guest spots by famous musicians and singers, such as Frank Sinatra Jr., David Lee Roth, and Nancy Sinatra, but none compare to the recurring appearance of music icon and lead singer of the Four Seasons, Frankie Valli. Valli made his first of seventeen appearances in “All Happy Families…” as the high-ranking capo of the Lupertazzi family, Rusty Millio, a cunning and ambitious addition to the series.
Despite only having limited experience as an actor, the Jersey-born singer gives a natural and restrained performance that hits a rare sweet spot of authenticity, irony, and thematic usefulness without ever coming across as forced. Compared to other guest stars, Valli’s real-life persona and his character on the show create an unsettling contrast that catches fans completely off guard. No one ever expected Valli to convey such a menacing and ruthless character, which, ironically, is what makes his performance not only one of the show’s most memorable but also solidifies Valli as one of the best guest stars in The Sopranos.
3
Robert Patrick as Davey Scatino
“The Happy Wanderer” Season 2, Episode 6 (2000)
Robert Patrick made his first appearance in Season 2’s “The Happy Wanderer” as a habitual gambler, Davey Scatino, who ends up being in serious debt to Tony. Known for playing villains and figures of authority, Patrick gained initial notoriety for his role in Die Hard 2, but his career didn’t take off until his breakthrough performance in Terminator 2: Judgment Day. Over the years, Patrick has starred in a string of box office hits such as Cop Land, Walk the Line, and Clint Eastwood‘s Flags of Our Fathers, while also making guest spot appearances in a variety of shows, including, most recently, Peacemaker and Jeremiah Dunmire in Tulsa King starring Sylvester Stallone.
Despite only appearing in three episodes, Patrick’s guest performance as Scatino is often singled out as one of the show’s best. Very few guest stars manage to stand toe-to-toe with Gandolfini, but Patrick does it by going smaller, not louder than his co-star, utilizing a nervous energy and pleading that perfectly contrasts Gandolfini’s character. Unlike the majority of the characters on the show, Scatino isn’t a mobster or a major antagonist, but instead an average, suburban family man whose downfall strikes a relatable chord with fans, so that, by the end, Scatino’s storyline is seen as a genuine tragedy rather than a plot device.
2
David Proval as Richie Aprile
“Toodle-F*cking-Oo” Season 2, Episode 3 (2000)
In “Toodle-Fu*king-Oo,” fans are introduced to one of the show’s first major antagonists, Richie Aprile, played by David Proval, whose performance is considered to be one of the show’s most terrifying and unforgettable guest star performances. Proval is best known for his role in Martin Scorsese‘s Mean Streets, starring Robert De Niro and Harvey Keitel, as well as his performance as Snooze in The Shawshank Redemption. The actor has also made guest appearances on several popular shows, notably The West Wing, Everybody Loves Raymond, and Boomtown.
Proval’s stillness, flat delivery, and sudden emotional shifts make Aprile an unpredictable player with an impenetrable poker face that puts every fan on edge. It doesn’t take long for fans to realize Aprile’s brutal nature, which he puts on full display within the first few minutes of his introduction, giving the show a new degree of unsettling intensity and uncertainty. While Aprile is a man of few words, Proval’s performance proves that a character who is simply sitting in silence can incite more fear in viewers than any big speech or display of melodrama could ever achieve.
1
John Heard as Vin Makazian
“Meadowlands” Season 1, Episode 4 (1999)
John Heard first appeared in Season 1’s “Meadowlands” as Vin Makazian, a corrupt detective and alcoholic who provides Tony with inside information and occasionally investigates people for the mob boss. Heard was a movie and TV actor who is universally recognized for his role as Peter McCallister in Home Alone and Home Alone 2: Lost in New York. He also appeared in a handful of other successful movies, including The Pelican Brief, Beaches, and Penny Marshall‘s Awakenings.
When fans meet Makazian, he’s an already broken man who conceals his self-loathing, depression, and paranoia with dark humor and crude jokes. Many fans consider Makazian to be one of the series’ most haunting side characters, who also set the grim moral tone for The Sopranos right from the start. In 1999, Heard’s show-stopping performance earned him an Emmy Award nomination for Outstanding Guest Actor in a Drama Series. Even though Heard only appeared for a short time, his performance as Makazian is hailed as a significant contribution to the show’s legacy, making Heard the best guest star in The Sopranos.
