What Happened To Diddy's Former Assistant, Fonzworth Bentley?

It all started with an umbrella.

In the early 2000s, Derek Watkins famously became known as Fonzworth Bentley, a play on the character Bootney Lee Farnsworth from the 1975 film Let's Do It Again, and assumed the role of an umbrella-toting, full-time butler for multi-million dollar producer Sean "Diddy" Combs.

It didn't take long for Bentley to grow his own brand and build a name for himself in television, music, and even literature. And while he may have put down the umbrella for greater pursuits, he definitely made his mark on pop culture during his time with Diddy, and made himself a hip-hop topic of conversation for years to come.

So how did this all happen?

The addition of Bentley to Diddy's entourage and his newfound persona were a result of the rapper needing to clean up his act after he was acquitted of gun possession and bribery charges from a nightclub shootout in 1999. The rebranding included Combs going by both Puff Daddy and P. Diddy, a whole new wardrobe and the inclusion of Bentley, the then 27-year-old Atlanta native.

In 2003, Fonzworth Bently made his grand appearance next to P. Diddy in Season 2 of Making The Band.

At first, the tall, dapper personal assistant made everyone question what exactly was happening, but soon enough Bentley became a pivotal part of getting the potential hip hop stars in line and ready to appear as distinguished gentlemen. The man formerly known as Derek slowly rose to fame as more and more hip-hop elites wanted to learn from his high level of style, fashion, and upper tier of sophistication. Thanks to his wealth of knowledge, Bentley went on to pen an etiquette book in 2007 titled, Advance Your Swagger: How to Use Manners, Confidence and Style to Get Ahead.

And the former valet even went on to land his own MTV reality show in 2008, From G's to Gents, where he taught wayward men the ways of being gentlemen.

By the time he snagged his own reality show, it was clear that Bentley's umbrella-carrying days were long gone. In fact, he went on to work with the likes of Kanye West, Gucci Mane, Andre 3000, the Black Eyed Peas, and many more.

Fonzworth isn't just a musician either, as he's appeared in many films over his career.

Bentley went from the small screen of reality television and music videos to the big screen, appearing in numerous films. He made his movie debut in 2003 in Honey alongside Meiki Phifer, playing a barber in Phifer's barbershop.

The following year he had a speaking role as a salesman in Fat Albert starring Kenan Thompson.

Bentley later worked with OutKast in 2006 in the star-studded, surrealistic musical Idlewild, where he voiced the drinking flask of Big Boi's slick-talking character Rooster. In 2017's Think Like A Man Too, the sequel to the movie adaption of Steve Harvey's controversial book Act Like A Lady, Think Like A Man, he made a cameo as a well-dressed shot caller. Describing his role he said,

"Kevin [Hart] needs to learn how to pay his bills, and if he don't pay his bills, there are people out here that aren't afraid to talk to him about that...and so that's what my character does in the film."

While he hasn't been in the spotlight as often recently, Bentley is still actively working, and working on building a family.

Bentley married actress Faune Chambers in 2010 and had two children, Daniel and Zoie. Professionally, in addition to having writing credits on a few Kanye West albums, including Yeezus and The Life of Pablo, Bentley has also written and produced songs for ABC's hit show Black-Ish as well as created choreography for the promotional video for the spin-off show, Grown-Ish.

And while Bentley's far from an umbrella-holding personal assistant these days, he and Diddy still seemingly have a good relationship. In 2019, he wished the mogul a happy birthday, and guaranteed an epic celebration worthy of Diddy's 50 years.

Over the years, through his debonair cameos in movies, music videos, and TV, Bentley has clearly solidified himself as a leader in giving hip-hop streetwear a flair of sophistication, umbrella or not.

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