After being snubbed by the Academy for decades, Martin Scorsese’s status as arguably the greatest living filmmaker was finally recognized with a Best Director win for The Departed. This Oscar was seen more as a lifetime achievement award to make up for past snubs, as The Departed isn’t considered to be on par with Scorsese’s true masterpieces, like Taxi Driver and Goodfellas. But it’s still a riveting cat-and-mouse thriller with a tense plot and captivating characters.

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Several years later, Scorsese reteamed with Leonardo DiCaprio for another complex, large-scale crime story, The Wolf of Wall Street, a pitch-black comedy about the stock trade that could be described as “Goodfellas meets The Hangover.” Both movies, like all of Scorsese’s works, have their fair share of memorable music moments.

The Departed: “Gimme Shelter” By The Rolling Stones

Jack Nicholson pointing a finger in The Departed

Martin Scorsese really likes “Gimme Shelter.” In addition to playing it a handful of times throughout The Departed, Scorsese has included the Rolling Stones hit in both Goodfellas and Casino.

It’s the first song that plays in The Departed, as Frank Costello’s voiceover narration is explaining how his Irish Mob organization operates in Boston’s criminal underworld.

The Wolf Of Wall Street: “Dust My Broom” By Elmore James

Leonardo DiCaprio talks to the camera in The Wolf of Wall Street

Before taking the audience back to the beginning of his career on Wall Street, Scorsese’s biopic of Jordan Belfort shows the infamous stockbroker at the height of his power.

Elmore James’ “Dust My Broom” plays on the soundtrack as he describes his lavish, excessive lifestyle directly to the viewer and the camera shows off his massive estate and sports car collection.

The Departed: “Comfortably Numb” By Roger Waters, Van Morrison & The Band

Billy Costigan Jr. in The Departed

While “Comfortably Numb” was originally recorded by Pink Floyd for their seminal album The Wall, the version that appears in The Departed was performed by Floyd’s Roger Waters, Van Morrison, and The Band.

The song plays as Costigan is filling out his forms as a “citizen” and goes over to Madolyn’s place. Scorsese previously directed a documentary about The Band called The Last Waltz.

The Wolf Of Wall Street: “Boom Boom” By John Lee Hooker

Margot Robbie in a restaurant in The Wolf of Wall Street

When Jordan Belfort takes his future wife Naomi out for dinner (while he’s still married to his first wife), she tells him they won’t be friends and he drives her home.

John Lee Hooker’s “Boom Boom” plays on the soundtrack before she Jordan is invited up to her apartment and they have sex.

The Departed: “Nobody But Me” By The Human Beinz

Billy fights two men in a bar in The Departed

Now best known for being lip-synced by the employees of Dunder Mifflin in an Office cold open, the Human Beinz’s “Nobody But Me” previously appeared on the soundtrack of The Departed. As two goons ask a shop owner for protection money and poke fun at the Irish, Costigan snaps and the song plays as he beats them up.

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He breaks his hand in the fight and has to wear a cast for a huge chunk of the movie before his arm is pinned to a table and the cast is ripped off.

The Wolf Of Wall Street: “Smokestack Lightning” By Howlin’ Wolf

Belfort motivates his employees during a company meeting

A lot of the most cinematic moments in The Wolf of Wall Street indulge in the mayhem of Stratton Oakmont’s corporate strategy. It’s much more fun to watch a slow-motion opera of debauchery than a dry lecture about stock pricing.

Howlin’ Wolf’s “Smokestack Lightning” plays as Jordan’s employees are celebrating their end-of-week profits with a bunch of strippers, cross-cut with the DEA investigating the company.

The Departed: “Baby Blue” By Badfinger

Jack Nicholson and Leonardo DiCaprio in The Departed

Badfinger’s “Baby Blue” was later used to terrific effect in the final scene of Breaking Bad, but The Departed used it first when Billy Costigan learns that Frank Costello is an FBI informant.

This plot point was inspired by Whitey Bulger, who was simultaneously one of the FBI’s most wanted criminals and an informant for the bureau.

The Wolf Of Wall Street: “Popeye The Sailor Man” By Sammy Lerner

Jordan Belfort wrestles the phone off Donnie since the FBI is listening to the conversations

Perhaps the most memorable sequence in The Wolf of Wall Street is when Jordan and Donnie take Quaaludes. After they don’t seem to have any effect, Jordan drives out to the country club to take a call. He finds out the FBI has tapped his phones right as the drugs start to hit.

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He desperately tries to get back to his car so he can drive home and stop Donnie from using the phones to talk shop. Back at the house, when Donnie is suffocating, Jordan takes some cocaine at the same time Popeye is eating some spinach on the TV and it has a similar effect on him. It gives him the boost of strength he needs to save Donnie’s life.

The Departed: “I’m Shipping Up To Boston” By Dropkick Murphys

Jack Nicholson and Matt Damon in The Departed

Most of Scorsese’s crime movies take place in New York, a city whose criminal underbelly he’s familiar with, but The Departed took him to Boston. He left behind the Italian Mafia to explore the Irish Mob.

Dropkick Murphys’ “I’m Shipping Up to Boston” went a long way toward defining this new identity. It plays over the title screen, and also during a handful of crucial moments throughout the movie.

The Wolf Of Wall Street: “Mrs. Robinson” By The Lemonheads

Kyle Chandler and Leonardo DiCaprio in the arrest scene in The Wolf of Wall Street

The Lemonheads’ cover of the ‘60s Simon & Garfunkel hit “Mrs. Robinson” plays as FBI agents march into the offices of Stratton Oakmont to make a triumphant litany of arrests.

Along with Sid Vicious’ rendition of “My Way” playing over the end credits of Goodfellas, this is a prime example of Scorsese using a punk version of an old-timey song to showcase the justice system at work.

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