Since bursting onto the rap scene in the early 1990s, Sean 'Diddy' Combs has adopted an array of different monikers. The now-disgraced rapper's first reinvention occurred in early 2001, shortly after he was acquitted of charges related to a nightclub shootout.

Desiring a fresh start, the now 54-year-old changed his name from Puffy to P. Diddy. Accompanying the new moniker was Fonzworth Bentley; a rather dapper umbrella-toting personal assistant and valet, presumably hired to lend more authenticity to the rapper's newly refined image.

Fonzworth's entry into Diddy’s inner circle caused quite the media frenzy, propelling the previously unknown butler to near-instant celebrity status. With his fanbase growing by the day, it wasn’t long before Fonzworth cast aside his umbrella to pursue his own music career. So, what exactly has the Fonzworth Bentley been up to since leaving Diddy’s employ?

Updated September 2024: This article has been updated to reflect the most recent information regarding Fonzworth Bentley and how his life changed after being Sean Combs' personal assistant. Fonzworth was not Diddy's assistant when he dated Cassie. It is unclear what Fonzworth witnessed as far as the sex trafficking charges Diddy has been charged with.

What Happened When Fonzworth Bentley Was Photographed Alongside Diddy In 2001?

Fonzworth Bentley being photographed with Diddy in 2001 became the biggest marketing campaign ever launched

Three-time Grammy winner Diddy was in the headlines quite a lot in 2001, just as he is in 2024 for his sex trafficking charges. The now 54-year-old rapper not only faced and triumphed over gun possession and bribery charges tied to a 1991 nightclub altercation, but he also underwent a radical metamorphosis, shedding the moniker, ‘Puffy’ to become ‘P. Diddy’ and embracing an air of cultivated elegance.

“No more Puff Daddy — the first week in June we’re gonna have a name change ceremony. I’m not doing it as serious as Prince [but] I just want something fresh. I’m rockin’ with ‘P. Diddy’ now."

Diddy went on to say, “My man Biggie gave me that name.”

With the new moniker firmly in place, the acclaimed rapper was ready to experiment with some other changes. Just months after shedding the name ‘Puffy,’ the rapper was photographed in St. Tropez in the company of a rather dapper umbrella-carrying gentleman; a man the world would later come to know as Fonzworth Bentley.

''That picture was the biggest marketing campaign that any unknown has ever launched,” Fonzworth would later say of the photograph in a 2004 interview with the New York Times.

“Jay Leno talked about that picture, so did Regis and Kelly. It was in Time, Newsweek, People. It made me famous overnight.''

How Did Fonzworth Bentley Land A Job As Diddy’s Personal Assistant And Valet?

Fonzworth Bentley sent Diddy inspirational Bible verses when Diddy was facing gun charges

As it later came to light, Diddy had crossed paths with Fonzworth, then going by his given name, Derek Watkins, at a soul food joint right in the midst of his gun possession and bribery trial. According to the New York Times, Fonzworth had taken it upon himself to send the rapper inspirational Bible verses while he grappled with the infamous charges.

A few months after Diddy's legal triumph, Fonzworth, who was managing a restaurant at Eleven Madison Park at the time, hit Diddy with an interesting message.

''Please don't make me go back to my hater boss.”

Shortly after that daring message, Diddy recruited Derek as his personal assistant and valet, christening him Fonzworth Bentley.

''I remember the day exactly,'' Bentley later shared with the New York Times. ''It's going to be in the movie about my life."

"Sean waved his hands in my face and said, 'Your life has just changed. Are you ready?'''

What Happened To Fonzworth Bentley After He Stopped Working For Diddy?

Fonzworth Bentley went on to write a best-selling book, started a music career, started an acting career, and collaborated with artists like Kanye West

Fonzworth Bentley’s life underwent a radical metamorphosis after he cast aside his umbrella and started pursuing his dreams of stardom. In 2003, Fonzworth landed a spot on Diddy’s MTV reality show, Making The Band, where he, yet again, beguiled fans with his sophisticated style and unflappable etiquette.

Soon after gracing the show, Fonzworth ditched his umbrella and started pursuing other opportunities.

Riding high on his escalating fame, Fonzworth secured a book deal and went on to author the New York Times best-selling etiquette book, Advance Your Swagger: How to Use Manners, Confidence, and Style to Get Ahead.

A few years later, Fonzworth secured his very own MTV show, aptly titled From G's to Gents. The show, which enjoyed a two-season run before bowing out in 2009, saw Fonzworth leveraging his profound knowledge of etiquette to guide misguided young men into the world of gentlemen.

But the show’s cancelation was merely a blip in Fonzworth’s rapid ascent to stardom. Just two years later, Fonzworth ventured into music, releasing his debut album, C.O.L.O.U.R.S. by Derek Watkins.

Two years after dropping his debut album, Fonzworth collaborated with Kanye West on his 2013 album, Yeezus, acquiring songwriting credits on multiple tracks, including "On Sight," "Black Skinhead," "I Am God," and "Hold My Liquor."

The duo would team up yet again for Kanye’s 2016 album, The Life of Pablo, where Fonzworth’s involvement earned him producer credits for the soul-stirring single, "Ultralight Beam."

"A Kanye album is like a working document. You don't hear the final version of it until it is available for purchase," Fonzworth said of working with West said in a 2016 interview with Fader.

"That's just the way it works. Every producer knows that, every friend knows that. That's just the way it is. I really admire that about him: his ability to strip down a genius idea and chase another genius idea that's come to light."

A man of many talents, Fonzworth has also dabbled in acting, gracing the silver screen with small yet impactful roles. Some of Fonzworth's projects, according to IMDb include:

Fonzworth's musical prowess also translated seamlessly to the small screen. Beyond writing songs for ABC’s hit comedy show, Black-ish, Fonzworth also masterminded the first-ever promotional video for the spinoff show, Grown-ish.

With lucrative opportunities practically pouring in from every corner, Bentley has amassed a considerable fortune. The former butler is currently worth about $2 million.

Fonzworth is also quite the family man, and is currently married to producer, Faune Chambers Watkins, with whom he shares two kids; a daughter named Zoie Alecia Watkins and a son named Daniel Watkins.