Diddy's 6 most cinematic music videos

Big budgets, superstar cameos, and all the elements that defined the golden age of hip-hop.

  /  06.26.2018

In a 2016 interview with Complex Hustle, mogul and entertainer Sean Combs shared that his formula to achieving success has been constantly reflecting on his purpose. Since then, his primary purpose has been to “inspire, create a platform and teach” in order to give those around him the opportunity to define their own success and achieve it. Listed by Forbes as the second wealthiest musician in the world, Combs has built a career on elevating those around him and exploring new frontiers of culture. The music industry has benefited enormously from his drive to push boundaries and innovate in his iconic music videos. Let’s explore some of his most cinematic visuals.


In the visuals for this lyrical masterpiece from his classic No Way Out, Combs channels his inner Blade. With the mood set by The Notorious B.I.G.’s menacing verse, this short action film imagines Puff as the protagonist. Complete with explosions and danger at every turn, Combs flips, jumps, and runs from the pursuing Feds. The video also features legendary rapper Busta Rhymes who, in a way only he could, looks dope as hell wearing a feathered fit as he raps from the top of a colossal statue.

“Shake Ya Tailfeather”

Straight from the soundtrack of Bad Boys 2, this track features southern rapper Nelly at the apex of his historic run. The visuals contain each element that defined the golden age of hip-hop videos: tropical locations, oversized colorful jerseys, black and brown women twerking to their hearts’ content, and—most importantly—fedora hats. Dressed in all-white and sporting his signature cigar, Combs performs one of the strongest verses of his career. This standout is one of the tracks that bridged the gap between Bad Boy’s longtime ride-or-dies and its newest fans.

“Been Around the World”

One of Combs’ greatest strengths has always been the ease with which he reinvents himself. Back when he was Puff Daddy, we knew the entertainer for being youthful—yet ahead of his time. This is the best way to describe perhaps the most creative video in his catalog. The elaborate skit includes Biggie lines as a secret code, rapper Ma$e and Combs on a private jet, cameos from Quincy Jones, Vivica Fox and Wyclef, and a top-secret mission to protect the princess, Jennifer Lopez. A rolodex of R&B artists and rappers have attempted to recreate this vibe at least once in their careers.

“I’ll Be Missing You”

Upon losing his best friend Biggie, Combs teamed with R&B singer Faith Evans (his widow) and group 112 to pay homage through song. The result was an instant classic. Taking an epic spill from his motorcycle to kick off the video, Combs reminds us how suddenly tragedy can strike. “I’ll Be Missing You” stands as one of the greatest tributes in music.

“It’s All About the Benjamins”

Combs is one of the most qualified people alive to teach us how to be a baller and shot caller, and this video proves it. While many rappers spend entire videos showcasing their money, these dope visuals feature images of $100 bills for all of 15 seconds. Instead, we are given images of how Puff makes his money. Apparently, it involves running through the jungle in white suits and performing in front of millions of raving fans on mosh pits of dirt. There’s a metaphor in here somewhere. You’ll enjoy these stunning visuals while you search for it.

“I Need a Girl Part 2”

Confused and broken-hearted in “Part 1,” Combs has bounced back in time for this video. Even worse, he brought Ginuwine with him this time for the hook. Set in Miami, a city he now literally and figuratively holds the keys to, the video showcases luxury cars, hovering helicopters, and a watch that shines brighter than most rapper’s chains. And of course, no Bad Boy video is complete without a minimum of two or three Diddy Bops.



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