Examples of Hip-Hop’s Fascination With Frank Sinatra

In a 2008 campaign for Ciroc Vodka, Diddy used Frank Sinatra’s music to embody the “sophisticated celebration’ of the liquor brand. The ad started off with Sinatra’s ‘Come Fly With Me’ playing in the background. The black and white ad also used one of Sinatra’s California homes. “Frank Sinatra is one of my heroes... I couldn’t imagine a spirit more appropriate for such occasions today than Ciroc, a brand that has become synonymous with celebration,” the rap mogul said.

Hov has referenced the renowned singer over the years, which was underscored on his song “My Way.” In his 2009 song “Empire State of Mind,” Jay-Z dubbed himself “the new Sinatra.” The rappers’s love of New York City—coupled with his incomparable impact on music—makes the comparison a compelling one.

In an interview with Variety earlier this year, Ice-T explained why he stopped making solo albums. “These kids got softer, and soft is not something I’m able to give audiences. The first word in hip-hop is “hip” so how something stays hip for over 10 years is difficult,” he explained before he used the “Come Fly With Me” singer as an example. “Besides, I still do my ‘Ice-T: Art of Rap’ shows, which is my legacy hip-hop. Think of it like seeing Frank Sinatra. You want to hear the classics.”

Produced and arranged by DJ Cappel and Smitty, the Notorious B.I.G. and Frank Sinatra mash-up mixtape “Blue Eyes Meets Bed Stuy” was released in 2006. The two have been deemed as the unofficial Kings of New York, with tracks including “Everyday Struggle” and “Little Green Apples, 10 Crack Commandments.”

Atlanta rapper and Drake collaborator Quentin Miller sampled Frank Sinatra for his 2016 song “Cliché.” The song that was used was the crooner’s “In the Wee Small Hours of the Morning.” Miller talked about the rumors when it came to ghostwriting while the song Sinatra served as the opening track on the 1955 album of the same name.

No Malice, who is best known as half of the hip hop duo Clipse, released his debut album Hear Ye Him in 2013. Although the emcee tells tales of a drug-ridden past—which pales in comparison to his personal redemption arc—the Frank Sinatra sampled song “June” proved to be a light amongst more serious anecdotes.

On his 2008 project entitled “I Got The Juice,” Atlanta rapper paid his respects to Frank Sinatra by making a song named after the late singer. “Frank Sinatra” sampled “I’m Gonna Live Till I Die,” in which Sinatra states: “I’m gonna live ‘til I die/I’m gonna laugh ‘stead of cry/I’m gonna take the town and turn it upside down/I’m gonna live, live until I die.”

In 2009, Young Money released the album We Are Young Money. One track on the project, “She is Gone,” samples Frank Sinatra’s “Farewell, Farewell to Love.” The song starts with Sinatra crooning “Farewell” several times before Lil Wayne asks “Where my old lady at? Where my h* where?” To those questions, Sinatra’s voice is sampled yet again to retort: “She’s gone.”

On Diggy Simmons’ 2009 album, The First Flight, he decided to sample Frank Sinatra’s “Softly as I Leave You” on the song “Classic Introduction.” The track serves as the album opener. “Yea, its the first flight,” Simmons rapped. “It’s that cool breeze music right there with them violins up on it.”

In 2015, a previously unreleased collaboration from The Game and Skrillex, called “El Chapo,” started circulating. It starts off with a sample of Frank Sinatra’s “Granada,” in which he called himself “the God, El Chapo.” The Game, who has proven quite the controversial figure over the years, referenced the infamous Mexican drug lord El Chapo Guzman on this particular track.

Actor Jim Belushi told TMZ he made Tupac Shakur a Frank Sinatra fan while filming the movie Gang Related together. “I influenced him. I turned him on to Frank Sinatra,” he stated. Marlon Wayans, who worked with Tupac on Above the Rim, directly compared the two icons. “Pac was eventually going to win some Academy Award,” Wayans said. “He was like a Frank Sinatra. He was that powerful. There was no ceiling.”

In 2016, the legendary emcee Slick Rick told NME: “I’ve never done karaoke before but I know a lot of Dionne Warwick songs. I sample ‘Walk On By’ in one of my songs, ‘Mona Lisa’. It’s like how people like Frank Sinatra, she’s like a female urban Frank Sinatra. She then passed her baton to Diana Ross.” The rapper also said he wants the Sinatra song “My Way” to be played at his funeral. “It’s powerful, it’s strong. It’s just the way he sang it, he sang it real beautiful.”

The FBI tracked Frank Sinatra for over 40 years, collecting thousand of pages about his words, movements and relationships. Sinatra denied being connected to the mob but was friends with Chicago mob boss Sam Giancana. In 2009, Jay Z told a Swedish interviewer why he admires the late singer. “It’s always good to compare yourself to people you look up to. Pretty much the way he lived his life and the parallels in how he affected the culture is what I strive to do..His [background] was a little tougher than mine — the Mob.”