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 – after assuming the role of an umbrella-toting, full-time butler for multi-million dollar producer Sean "Diddy" Combs. For a point of reference, it happened somewhere between the rapper going by Puff Daddy and P. Diddy

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 being "acquitted of gun possession and bribery charges stemming from a nightclub shootout in 1999," per The Fader. Along with the re-branding came a new wardrobe and the then 27-year-old Atlanta native as a proper usher for Diddy into the world of being a sophisticated gentleman.

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

Fonzworth Bentley first appeared on an episode of 'Making The Band 2'

According to Vix, in 2005, Fonzworth Bently made his grand appearance next to P. Diddy in Season 2 of Making The Band. Initially, the tall, dapper personal assistant made everyone question what exactly was happening, but soon enough Bentley became a pivotal part of getting the potential R&B stars in line and ready to appear as distinguished gentlemen.

The personal assistant slowly rose to fame as more and more hip-hop elites wanted to learn more from Bentley's high level of style, fashion, and upper tier of sophistication. Thanks to his wealth of knowledge, the former valet 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 Bentley is actively working in the music and entertainment industries

Fonzworth Bentley went on to pen an etiquette book in 2007 titled, Advance Your Swagger: How to Use Manners, Confidence and Style to Get Ahead. "Bentley attributes his accomplishment to one key equation: Manners + Confidence + Style = Swagger," per the book description. "With this formula, Bentley transformed himself into an icon of unflappable grace, elegance, and good manners–and now he's on a mission to help you step up your game, advance your swagger, get ahead, and live out your dreams."

After making a name for himself and stepping out of Diddy's shadow, the fashion trendsetter transitioned into music professionally while he grew his family personally. Bentley married actress Faune Chambers in 2010 and had two children, Daniel and Zoie. 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, per TheBoomBox.

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, writing, "#thisis50 will be epic!"

Fonzworth Bentley appeared in many films, sans umbrella

Fonzworth 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, Jessica Alba, and Romeo Miller (formerly Lil' Romeo). He played 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 Steven Harvey's controversial book Act Like A Lady, Think Like A Man he made a cameo as a well-dressed shot caller.

"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," he told HipHollywood, adding, "and so that's what my character does in the film."

Over the years, through his debonair cameos in movies, music videos, TV, and of course his umbrella, Bentley solidified himself as a leader in giving hip-hop streetwear a flair of sophistication.