The 20 Best Musical Moments on 'The Sopranos'

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Steven Van Zandt, James Gandolfini and Tony Sirico on The Sopranos.

When The Sopranos’ creator David Chase was hand-selecting the music for his celebrated show, he had an epiphany -- real life doesn’t have a perfect soundtrack. “The songs can’t all be good, because life isn’t like that,” he told Noisey in 2015. “I’ve seen people [in TV] do this, where every song is a cool song. It takes you out of the moment.”

This reverence for all kinds of music is the beating heart of The Sopranos. Twenty years ago this Thursday (Jan. 10) marks the premiere of the show’s pilot episode, introducing the world to New Jersey mob leader Tony Soprano’s crime family and abode -- as well as cuts from Annie Lennox, Bo Diddley, Sting and Nick Lowe.

The Sopranos’ musicality begins with Steven Van Zandt, Bruce Springsteen’s longtime guitarist who plays consigliere Silvio Dante on the show. Back in 1999, Van Zandt had no prior acting experience, but he aced the audition for other reasons. “There was something about the E Street Band that looked like a crew,” Chase remembered.

From that casting choice, Chase went on to loosely handpick music that Tony -- a New Jersey dad in his 40s -- would have enjoyed in his youth or young adulthood. But on The Sopranos, rules were made to be broken. Binge the series from front to back, and you’re treated to a mini-history of 20th century music.

From ‘50s vocal jazz (Benny Goodman, Dean Martin, Frank Sinatra) to kick-the-tires classic rock (The Kinks, The Rolling Stones, Van Morrison) to pounding metal (Slipknot, and, famously, Mudvayne) to trippy, ambient ‘90s material (Moby, Radiohead and Mazzy Star), The Sopranos’ soundtrack is uniquely omnivorous from beginning to end.

And for the show’s famous final scene, Chase had viewers drink straight from the bottle. As Tony eats onion rings with his family, Journey’s anthemic “Don’t Stop Believin’” plays on the jukebox, building steadily until the scene -- and series -- cuts to black. Fans are still up in arms about the meaning of this controversial ending; but as with the rest of The Sopranos, it’s all about the tunes.

In honor of The Sopranos’ 20th anniversary, here are its 20 most well-placed musical moments, ranked.

20. Al Green, “Take Me to the River” (“Second Opinion”)

In the Season 3 episode “Second Opinion,” Tony is unamused by a Billy Bass that bartender Georgie puts in his office at the Bada Bing strip club. The gag gift sings Al Green’s 1974 soul hit “Take Me to the River” -- a morbid reminder of Salvatore “Big Pussy” Bonpensiero, Tony’s enforcer who he was forced to bury at sea in the previous season.

19. Frank Sinatra, "Nancy (With The Laughing Face)” (“Watching Too Much Television")

A brilliant choice because it’s never explained: In the Season 4 episode “Watching Too Much Television,” the crew holds a welcome-back party for capo Paulie “Walnuts” Gualtieri after he’s released from jail. “My song,” remarks Paulie when Frank Sinatra’s version of (“Nancy (With the Laughing Face)” pipes into the gathering.

This 1942 ballad was originally written by Phil Silvers and retitled in tribute to Sinatra’s daughter; why would a childless, self-absorbed criminal be so moved by “Nancy”? Mafioso Bobby Baccalieri’s bewildered reaction is genius: “What the f---? Why is this your song?”

18. The Four Seasons, “Dawn (Go Away)” (“Christopher”)

The legendary New Jersey pop star Frankie Valli was no stranger to the mob -- and looms large over The Sopranos, from a peppering of dialogic references to literally appearing as mobster Rusty Millio, nicknamed “The Mayor of Munchkinland.”

In the Season 4 episode “Christopher,” Tony and Silvio have a passionate debate about Italian-American identity. “You take it up with Frankie Valli when you talk to him!” spits Tony at the end -- and Valli and the Four Seasons’ “Dawn (Go Away)” wafts in over the closing credits. “It had to do with that whole thing Tony's telling Silvio about class differences,” explained Chase about this cleverly Valli-assisted scene.

17. Frank Sinatra, “It Was a Very Good Year” (“Guy Walks Into a Psychiatrist’s Office…”)

Season 2’s premiere begins with a long montage featuring the status of every major character, soundtracked by Frank Sinatra’s ruminative “It Was a Very Good Year.” This would prove to be a dry-humored choice, being that the viewer is treated to shots of Tony’s deceitful Uncle Junior behind bars and his caustic mother Livia hospitalized for a stroke.

16. Henry Mancini/The Police, “Peter Gunn”/”Every Breath You Take” (“Mr. Ruggerio’s Neighborhood”)

It was Chase’s wife, Denise, who came up with the best musical moment in the Season 3 premiere “Mr. Ruggerio’s Neighborhood.” “You know that ‘Every Breath You Take’ and the ‘Peter Gunn’ theme are the same song?” she reportedly said to her husband.

The Sopranos’ team matched up the key and BPM of both songs, and it worked: “Peter Gunn” represented the long arm of the law, and “Every Breath You Take” suggested a stalker’s surveillance. It was a killer mashup idea for a wiretap-centric episode.

15. Tindersticks, “Tiny Tears” (“Isabella”)

Tindersticks’ downer classic “Tiny Tears” appears twice in Season 1’s “Isabella” -- first when Tony lies in his bed under the influence of prescription lithium, and again when Junior executes a failed hit on Tony.

That latter scene was written specifically to pair with “Tiny Tears”; from Tony buying orange juice in a Godfather homage to one of his would-be assassins accidentally whacking another, it’s perfection.

14. Jefferson Airplane, “White Rabbit” (“Down Neck”)

If “White Rabbit” has become tired shorthand in TV and film for a drug experience, The Sopranos cleverly subverts this cliché. The Jefferson Airplane hit cues up twice in Season 1’s “Down Neck,” both during Tony’s Prozac-fueled flashback to his mob-captain father and a lighthearted scene in which he and his son A.J. make ice cream sandwiches.

In this parallel usage, “White Rabbit” manages to connote something deeper than pill-popping: what fathers pass on to their sons.

13. Tom Petty and the Heartbreakers, “American Girl” (“Join the Club")

While Tony is laid up in a coma in “Join the Club,” Carmella delivers a touching speech to her husband. “You’re strong as a bull,” she says, recalling the early days of their courtship in which he “used to pick me up and throw me over your shoulder.” Tom Petty and the Heartbreakers’ “American Girl” plays on a nearby portable stereo.

“And for one desperate moment / He crept back in her memory,” sings Petty on his signature tune. It’s apropos for a scene in which Carmella is lost in the past.

12. Material feat. William S. Burroughs, “Seven Souls” (“Members Only”)

Season 6 begins with a two-year time jump and a montage of major life changes: Bobby and Tony’s sister Janice are raising a baby, A.J. is in college and Tony’s capo Ray Curto is on borrowed time from a fatal stroke.

This glimpse into the cycle of life is well-soundtracked by acid-jazzers Material’s collab with William S. Burroughs, “Seven Souls,” in which the author drones about Ren, Sekem and other Egyptian spirits that leave the body when you die.

11. John Cooper Clarke, “Evidently Chickentown” (“Stage 5”)

Tony’s cousin Tony Blundetto is released from prison at the top of Season 5, sparking a chain of revenge when he guns down crime family boss Phil Leotardo’s brother Billy. When Leotardo pays his respects to his late brother, he fumes over the indignities his family has suffered -- and the obscure British post-punker John Cooper Clarke’s seething “Evidently Chickentown” nails his frustration perfectly.

10. Nils Lofgren, "Black Books” (“Second Opinion”)

Another great song choice in “Second Opinion": Nils Lofgren’s 1995 track “Black Books” is used for two scenes centered around Tony’s wife Carmella. First, the song plays as she visits their daughter Meadow at Columbia, and again when she gets Tony to donate a large sum of money to her school.

“It’s just a beautiful song,” Chase later marveled. “Nils’ guitar playing is luminous.” He’s right: with its dreamily dated ‘90s production, “Black Books” adds an ethereal undertow to these quiet moments.

9. The Chi-Lites, “Oh, Girl” (“Watching Too Much Television”)

In Season 4, Tony’s Russian ex-mistress Irana Peltsin moves on to Ronald Zellman, a New Jerseyan congressman. Initially giving his blessing, Tony gets other ideas when he hears the Chi-Lites’ 1972 R&B classic “Oh, Girl” on the radio -- and uncharacteristically tears up.

Inflamed with jealousy, he immediately drives to Irana’s apartment and emasculates a boxers-clad Zellman by beating him with a belt. “If you're driving along, late at night and that song comes on, it gets you,” said Chase. That’s an understatement when it comes to “Watching Too Much Television.”

8. Time Zone, “World Destruction” (“For All Debts Public and Private”)

The snotty, nihilistic “World Destruction,” a collaboration between Afrika Bambaataa and John Lydon, bookends the Season 4 premiere “For All Debts Public and Private.” It first tracks when Tony checks his mail, and again when Christopher enacts revenge on the crooked cop who killed his father at a young age.

This episode was written the week of the September 11 attacks, lending itself to this politically abrasive, no-holds-barred tune’s inclusion. “It has that feeling of end times,” Chase commented. “A feeling of ‘Where are we going, how did we get here?’”

7. Roger Waters feat. Van Morrison and The Band, “Comfortably Numb” (“Kennedy & Heidi”)

Tony’s protégé Christopher meets his end in Season 6’s “Kennedy & Heidi,” when he intoxicatedly flips his Escalade off a steep embankment -- with Tony inside. Noticing that a tree branch had impaled an empty child’s car seat in the back, Tony opts not to call 911 and to quietly kill an already badly wounded Christopher by suffocation.

Right before a distracted Christopher runs off the road, he fumbles the soundtrack to the recent gangster-focused film hit The Departed into the CD player -- beginning with Roger Waters, Van Morrison and The Band performing the drug-themed power ballad “Comfortably Numb.” Before Tony’s beloved “nephew” reaches the end of his life and his mentor’s expectations, we hear the money line: “The child is grown / The dream is gone.”

6. The Rolling Stones, “Thru and Thru” (“Funhouse”)

In “Funhouse,” Tony, Silvio and Paulie confirm their suspicions: Salvatore “Big Pussy” Bonpensiero, their once-trusted enforcer, has been an FBI informant for some time. A food poisoning-stricken Tony has a fever-dream of a talking fish, representing Big Pussy and admitting to flipping. Later, he searches his old friend’s bedroom, finding a listening device in a cigar box.

The Rolling Stones’ sparse Voodoo Lounge cut “Thru and Thru,” an uncharacteristically emotional cut sung by Keith Richards, soundtracks the hard decisions made in “Funhouse.” It follows the guys from their final meal with Pussy to a climactic scene in which they gun him down and dispose of his body in the ocean.

5. Moby, “When It’s Cold I’d Like to Die” (“Join the Club”)

In the throes of dementia, Junior shoots Tony at close range in his home in “Members Only” -- leaving him unconscious in the following episode “Join The Club.” What follows is a surreal dream sequence from a comatose Tony, in which he hallucinates he’s a Precision Optics salesman who accidentally assumes the identity of a Kevin Finnerty.

After getting into a scuffle with irate Buddhist monks and suffering a concussion after falling down hotel stairs, dream-Tony settles into his room, picks up the phone and hangs up before dialing. The ambient strains of Moby’s “When It’s Cold I’d Like to Die” flow into the scene, gorgeously driving home Tony’s existential crisis while on the verge of death.

4. Andrea Bocelli, "Con te partirò” (“Commendatori”)

In a 2019 interview with the New York Times, Chase singled out the one episode of The Sopranos that he’d like to redo. “The show when they went to Italy,” he said, referring to “Commendatori” from Season 2. “That really wasn’t our element. We didn’t know what we were talking about.”

Regardless of the cultural accuracy of “Commendatori,” it contains one of The Sopranos’ all-time great musical moments, courtesy of Andrea Bocelli. His signature song, "Con te partirò” (a hit in English as “Time to Say Goodbye”) plays three times in the episode, most strikingly while Carmella and Big Pussy’s wife Angie Bonpensiero have dinner in Vesuvio.

“That song worked emotionally without you understanding what [Bocelli] was saying.” said Chase. “What that meant for Carmela was, ‘I want to be anywhere but here. I don’t want my life. I want a different life.’”

3. The Kinks, “Living on a Thin Line” (“University”)

In the Season 3 episode “University,” mobster Ralph Cifaretto has an affair with Tracee, a dancer at the Bada Bing who subsequently becomes pregnant with his child. When she humiliates Ralph in front of his crew, he beats her to death -- and incites a similar assault from Tony.

This unflinchingly violent episode is bookended by the Kinks’ “Living on a Thin Line,” a relatively obscure single from the British Invasion greats, sung by Dave Davies. “All the wars that were won and lost  Somehow don’t seem to matter very much anymore,” he sings: which conflicted crook does this remind you of?

In “University,” the moody “Living on a Thin Line” does more than add heft to any given scene: it defines the length and breadth of The Sopranos’ psychological grey areas.

2. Journey, “Don’t Stop Believin’” (“Made in America”)

The final scene of The Sopranos’ series finale remains controversial for what it doesn’t show. Since its 2007 airdate, the cut-to-black ending of “Made in America” has spawned fierce communion among the show’s fanbase. Who are the diner customers? Why remember the “good times”? Is Tony alive or dead, anyway?

But none of it would quite have the heft without Journey’s most ubiquitous hit, cranked on the jukebox by Tony himself. Debates aside, the way the ‘80s standard builds as the various Sopranos arrive one by one is still a choreographed sight to behold. And A.J.’s exhortation to “remember the good times” dovetails beautifully with the song’s message.

We may never know the true fate of Tony Soprano -- Chase himself declared in 2019 that there’s no correct answer. But as with The Sopranos’ litany of classic song choices, all you need to know is right there in “Don’t Stop Believin’.”

1. Van Morrison, “Glad Tidings” (“All Due Respect”)

When it comes to sparking debate and enduring in the cultural memory, no Sopranos musical choice comes close to “Don’t Stop Believin’” in the finale. Van Morrison’s cheery “Glad Tidings,” which plays right before Tony blows his cousin Tony Blundetto away with a pump-action shotgun, is merely perfect.

First, there’s the intent: Tony is forced to whack his cousin not out of vengeance, but mercy. With Phil Leotardo out to avenge the death of his brother, Tony decides to spare Blundetto potential torture by slaying him in one clean shot. “I’ll send you glad tidings from New York,” Morrison sings before Blundetto is hit with buckshot, eventually ending with “Hope you’ll come right on time.”

The Sopranos’ soundtrack had never quite nailed this level of dark-humored detail before, and that’s why "Glad Tidings" stands alone as No. 1. A head-nodding, singalong rocker meeting a morbid scene -- that’s Chase’s vision at its purest.

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