Very few musicians have made as much of an impact as Frank Sinatra. The iconic crooner has sold over 150 million records across the world, won 18 Grammy Awards including the Lifetime Achievement Award, and was named one of the most influential people of the 20th century by Time magazine. He even received the Presidential Medal of Freedom from Ronald Reagan.
With directors ranging from Martin Scorsese to Steven Spielberg counting themselves as Sinatra fans, the singer’s work has been included in a ton of memorable movie moments. Sinatra can be heard in such classics as Goodfellas, When Harry Met Sally, and Fear and Loathing in Las Vegas.
“South Of The Border” In We’re The Millers
Jason Sudeikis stars in We’re the Millers as a cannabis dealer who’s tasked with crossing the border to pick up a marijuana shipment in Mexico. He hires a stripper and two abandoned youths to pose as his family to avoid looking suspicious.
Frank Sinatra’s “South of the Border” is aptly paired with the fake Miller family’s journey across the border into Mexico to pick up the product.
“That’s Life” In Joker
Todd Phillips’ Joker was heavily influenced by the work of Martin Scorsese — specifically Taxi Driver and The King of Comedy — so it’s appropriate that he featured one of Scorsese’s favorite singers on the soundtrack. Frank Sinatra’s “That’s Life” plays over Joker’s ambiguous final scene as Arthur runs through Arkham Asylum, pursued by orderlies.
Stephen Sondheim's “Send in the Clowns” is integral to the shocking subway murder scene, as the suits sing it to Arthur before being shot dead, and the Sinatra rendition of the song plays over the movie’s end credits.
“You’re Getting To Be A Habit With Me” In Fear And Loathing In Las Vegas
Terry Gilliam’s delightfully surreal film adaptation of Hunter S. Thompson’s Fear and Loathing in Las Vegas has a heck of a soundtrack, including hits by Bob Dylan, the Yardbirds, Buffalo Springfield, Jefferson Airplane, and Tom Jones.
The movie also features a song by Frank Sinatra. It’s appropriate that a movie about two people taking a bunch of drugs would use “You’re Getting to Be a Habit with Me.”
“The September Of My Years” In Bringing Out The Dead
One of Scorsese’s most underrated psychological thrillers, Bringing Out the Dead stars Nicolas Cage as an ambulance driver. In one scene, paramedics are treating a man named Mr. Burke and when it becomes apparent he’s not going to make it, they tell the family to play a song he liked.
So, they play “The September of My Years” by Frank Sinatra, which is about how quickly life passes by and death arrives sooner than we expect it to.
“High Hopes” In Rocky Balboa
Sinatra’s “High Hopes” is the song that the titular boxer plays to enter the ring in Rocky Balboa. The song was chosen by Paulie, and while Rocky was initially skeptical, he later warmed to it.
When Balboa is about to enter the ring, the announcers blare Sinatra’s original 1959 recording of the song from the venue’s speakers.
“Come Fly With Me” In Catch Me If You Can
Steven Spielberg’s Catch Me If You Can is one of the funniest biopics ever made, starring Leonardo DiCaprio as conman Frank Abagnale Jr., who scammed his way into jobs like doctor and lawyer when he was a teenager.
For the scene in which Abagnale poses as a pilot and lands a regular paycheck from an airline, Spielberg aptly played Frank Sinatra’s “Come Fly with Me” on the soundtrack.
“Something Stupid” In Ratcatcher
Lynne Ramsay’s directorial debut Ratcatcher is a phenomenal movie, but since it revolves around a child living with the guilt of accidentally killing another child, it’s pretty challenging.
Throughout the movie, the boy’s mother plays records for the kids. One of them is “Something Stupid,” recorded by Frank and Nancy Sinatra.
“Summer Wind” In Blade Runner 2049
Before becoming a huge star with the lead role in Knives Out, Ana de Armas gave an unforgettable supporting turn as Officer K’s holographic girlfriend Joi in Denis Villeneuve’s surprisingly satisfying sequel Blade Runner 2049. In one scene, K plays Sinatra’s “Summer Wind” for Joi.
The movie also uses another Sinatra song. K plays “One for My Baby (And One More for the Road)” on a jukebox and a little hologram of Sinatra appears to sing it.
“It Had To Be You” In When Harry Met Sally
Rob Reiner struggled to come up with a title for his rom-com masterpiece When Harry Met Sally. At one point, he considered naming it after “It Had to Be You,” which acts as a sort of a theme song for the movie.
The director plays a few versions of the tune throughout the movie, including a rendition by Frank Sinatra. The song was originally written by Isham Jones (music) and Gus Kahn (lyrics).
“My Way” In Goodfellas
At the end of Goodfellas, Henry Hill has turned on all his friends in the mafia and resigned to a mundane suburban existence as a federal witness. In the final scene, he comes out of his house to get the paper and Scorsese foreshadows his fate — and the fate of everyone who gets involved in organized crime — with a shot of Joe Pesci firing a pistol at the camera against a black background.
Henry slams his front door to the sound of jail bars clattering shut and Sid Vicious’ cover of the Sinatra hit “My Way” plays over the closing credits.