Sean “Diddy” Combs transformed the entertainment industry in the ‘90s and early 2000s, releasing banger after banger under Puff Daddy. His record label, Bad Boy Records, signed some of the most prominent musicians of the time, including the Notorious B.I.G., Mary J. Blige, Faith Evans, and Usher. As a result, Diddy had a hand in creating many hit songs during the height of the TRL era.
Before he was Diddy, he went by the names P. Diddy, Puff Daddy, and Puffy. When he wasn’t surprising his fans with a new stage name, Diddy was building his empire as a music producer, actor, fashion designer, and entrepreneur.
Today, he is one of the wealthiest musicians in the world, with a handful of award-winning songs under his belt. Here’s a look at Diddy’s most iconic music videos.
6. ‘Mo Money Mo Problems’
Since its release in 1997, “Mo Money Mo Problems” by the Notorious B.I.G. featuring Mase and Puff Daddy has become one of the most popular songs in hip-hop history. Even though Biggie died before the song was released, creators found other ways to include him in the music video.
The futuristic sets, flashy wardrobe, and inclusion of Biggie’s interview clips left a lasting impression on fans. The song wound up at the top of the Billboard Hot 100 for two weeks, making Biggie the only artist in Hot 100 history to have two No. 1 singles after their death.
Even though he didn’t live long enough to experience his album’s success, Diddy has always strived to keep his friend’s memory alive.
5. ‘Been Around The World’
Long before Beyoncé’s “Lemonade,” there was Diddy’s 10-minute extended video for “Been Around The World.“ The song, featuring Mase and Biggie, was released in 1997 alongside an action-packed cinematic music video.
If the sight of Diddy on the toilet and jumping out of an airplane isn’t enticing enough, you may enjoy the cameos made by Quincy Jones, Vivica Fox, Wyclef, and Jennifer Lopez. Filmed before they were a couple, Lopez plays a princess in the music video who leads Diddy in a steamy candle-lit salsa dance.
4. ‘Victory’
Diddy’s 1998 song “Victory” featuring Busta Rhymes is iconic for incorporating the last two verses ever recorded by Biggie, captured the day before he died. The “Victory” music video is another cinematic masterpiece. It shows Diddy in a dystopian future, running from militia police in an action-packed pursuit.
Busta appears in the video as a feathery gargoyle overlooking the chase from the roof of a building. Actors Dennis Hopper and Danny DeVito also make cameos.
3. ‘Shake Ya Tailfeather’
Diddy’s music video for the hit single “Shake Ya Tailfeather,” featuring Nelly and Murphy Lee, embodies all of the trends from the early 2000s. Between the tropical setting, oversized jerseys, and plethora of fedoras, it’s no surprise that fans were quick to make this song their summer anthem.
The video’s choreography alone is enough to get anyone on their feet, shaking their tail feathers like it’s the turn of the millennium. Released in July of 2003, “Shake Ya Tailfeather” was featured on the Bad Boys II soundtrack and incorporates various scenes from the film in the music video.
2. ‘Bad Boy for Life’
Diddy’s music video for “Bad Boy for Life,” featuring Black Rob and Mark Curry, used humor to address important race and social issues. It starts with Diddy buying a home in “Perfectown, USA,” an unmistakably all-white suburban community. Diddy rolls up in a tour bus with 40 or so of his closest friends and family members for an out-of-this-world celebrity-fueled house-warming party.
To the dismay of his new neighbors, Diddy rocks out in his garage with Travis Barker and Dave Navarro, hits some golf balls off his roof with Derek Watkins, and shoots some hoops with Shaquille O’Neal. Other celebrity cameos that made this music video iconic include Ben Stiller, Snoop Dogg, Mike Tyson, Xzibit, and Ice Cube.
1. ‘I’ll Be Missing You’
“I’ll Be Missing You,” featuring Faith Evans and 112, is unquestionably Diddy’s most impressive creation. The touching tribute to the late Notorious B.I.G. won a Grammy Award for Best Rap Performance by a Duo or Group and spent 11 weeks at the top of the Billboard Hot 100 chart.
The music video is a moving reminder of how sudden things change and how fragile we are. Despite the controversy surrounding the song’s use of samples from The Police’s song “Every Breath You Take” without permission, it remains a classic.
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