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Diddy’s 5 Best Songs Ever

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By Jonathan Hailey

Rapper/mogul Sean “Diddy” Combs premiered his latest single “Workin” this week (Oct. 13) during the BET Hip-Hop Awards. Featuring Lil Kim, King Los, and Styles P, “Workin” has a throwback feel, due in part to the horn stabs. Since the man formerly known as Puff Daddy and P.Diddy wants that old sound back, it made us realize just how many hits he’s graced us with over the years. Let’s take a look back at five of Diddy’s best songs.

Puff Daddy feat. Faith Evans and 112 – “I’ll Be Missing You” (1997)

In the late ’90s, Diddy’s signature production style was taking hits from the ’80s and making them sound dope enough for everyone to want to dance and party to. With “I’ll Be Missing You,” he used a sample of the Police’s “Every Breath You Take,” a song about a  deranged stalker as the basis for a heartfelt tribute for his slain best friend and arguably one of the greatest rappers ever to touch a mic, Biggie Smalls. The song stayed in heavy rotation on the radio and was only elevated when he performed it at the MTV Video Music Awards. He came out draped in all white doing his Diddy bop and surprised the world by getting Sting to perform alongside him, Faith Evans, and 112.

Puff Daddy feat. Lil Kim, The Lox, and The Notorious B.I.G. – “It’s All About the Benjamins” (1998)

If you don’t know anything about Sean Combs, please know he’s about his paper. He’ll get it by any means necessary, which translates to handing out some of the toughest contracts in the business. He gave a hint to exactly how much of a paper gangsta he is when he released the song “It’s All About the Benjamins.” Diddy recruited The Lox, Lil Kim, and a posthumous verse from The Notorious B.I.G. for a hard knocking ode to stacking $100 bills. While Diddy was trying to talk about getting money, he had fans looking for the nearest Italian restaurant because of that three-course meal: spaghetti, fettuccine and veal. Even then, Diddy was still keeping it real in the field.

Related: Diddy Changes Name Back to Puff Daddy, Announces New Album

P.Diddy feat. Black Rob and Mark Curry – “Bad Boy 4 Life” (2001)

Rap music is the only genre where you’ll be crucified if you don’t write your own verses. Diddy has been the exception to the rule since he debuted in 1997. Everybody knew he used ghostwriters, but his delivery and overall songs were so good, we allowed him  to slide. The ghostwriter conversation came up again and Sean Combs ethered every single last one of his critics with nine words. “Don’t worry if I write rhymes, I write checks.” It was the dopest and most PG way of telling haters to kiss his a–. It also proves he means what he says because Bad Boy Records just signed a new distribution deal with Epic Records because they can’t stop and won’t stop. Take that, Take that.

P. Diddy feat. Ginuwine, Mario Winans and Loon – “I Need A Girl (Part 2)” (2002)

A year after their breakup, Combs was still pining for his ex-, Jennifer Lopez. They sent messages back and forth through their songs during that time. He put out “I Need A Girl (Part 1)” begging for her to come back. Lopez was having none of it and released the kiss off “Ain’t It Funny” with Ja Rule and Cadillac Tah. Diddy decided to double down on winning J. Lo back and put out a second version of “I Need A Girl” that boasted contributions from R&B stars Ginuwine and Mario Winans. Bad Boy artist Loon even made an appearance. The song became a smash hit, and yet Jennifer Lopez still didn’t cave in. In fact, she married and divorced dancer Cris Judd before this song fell off the charts. So point goes to Diddy on that.

Diddy feat. Keyshia Cole – “Last Night”

By the time 2007 rolled around, Diddy hadn’t had a hit to call his own in a while. R&B Princess of Heartbreak and Pain Keyshia Cole helped change all of that. The song told the story of a man going through all of the feels during the aftermath of a hard breakup and wanting to reconcile, but not wanting to be the first to wave the white flag. Fans related because who hasn’t wanted to call and make up with an ex- after a fight, but their pride is too big of a pill to swallow. Cole made the heartache palpable by singing with so much power you could hear her almost rupture a vocal chord during the hook. We all just wanted to dance away the heartbreak whenever “Last Night” played in the club.


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