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The shocking reports that Andre Harrell had died immediately made me reflect on his relationship with Diddy, who got his first official shot working in the music industry courtesy of the man who would become his mentor and provide a blueprint for the hip-hop music executive role he helped pioneer.

Harrell famously hired — and fired — a young Sean Combs who went by the name Puffy at the time. Working as an intern for Uptown Records, the label founded by Harrell, Puffy would be promoted to a lofty spot leading the company’s A&R team. It was a position that allowed him to sign iconic singers and rappers whose music recorded in the early 1990s went on to become timeless.

MORE: Condolences Pour In For Andre Harrell As Legendary Music Executive Dies At 59

Harrell later fired Puffy from Uptown, which was major industry news at the time considering Puffy brought the then-rising careers of hitmakers like Mary J Blige, Jodeci and a young Biggie Smalls to the record label. The firing was for Puff’s own good, Harrell said on the documentary about Diddy’s own Bad Boy Records label.

“When Puff got fired, he was on payroll, and his artists were on payroll, he’s still recording his artists, and he was able to find the best deal,” Harrell said in a scene from the documentary released in 2017. “So, I never fired him to hurt him, I fired him and basically made him rich.”

The rest, as they say, is history, as Puff-turned Puff Daddy-turned Diddy and Bad Boy went on to sell tens of millions of records and still remains a relevant force in music if not only because of the gravitas of its owner.

Through it all, though, Diddy and Harrell remained friends and colleagues, as shown in 2017 when the two of them sat down together for an interview for Revolt TV, the network owned by Diddy and vice chaired by Harrell.

It’s arguable that without Andre Harrell there would not be a Diddy; at least not possibly as well all know him today. Many times for young, budding entrepreneurs who happen to be Black, it takes that extra helping hand to take a chance on someone who shows glimmers of genius. Harrell did just that with a young Puffy, who dropped out of Howard University to and took a leap of faith in hopes of jump-starting his career in the music industry.

In honor of Harrell’s life and the extraordinary professional and personal bond he built with Diddy, scroll down to see some of their most iconic photos together through the years, complete with Harrell’s omnipresent and magnetic smile.

1. Heavy D File Photos

Heavy D File Photos Source:Getty

2. Sean “P. Diddy” Combs’ Fourth of July East Hampton Party

Sean "P. Diddy" Combs' Fourth of July East Hampton Party Source:Getty

Sean “P. Diddy” Combs and Andre Harrell during Sean “P. Diddy” Combs’ Fourth of July East Hampton Party at The Resort in East Hampton, New York, United States. (Photo by Johnny Nunez/WireImage) people,arts culture and entertainment,horizontal,usa,males,two people,sean combs,new york state,east hampton,tourist resort,andre harrell

3. Andre Harrell’s Birthday Party

Andre Harrell's Birthday Party Source:Getty

Andre Harrell and Sean ‘P Diddy’ Combs during Andre Harrell Birthday Party at 17 in New York City, New York, United States. (Photo by Johnny Nunez/WireImage) celebrities,arts culture and entertainment,horizontal,party – social event,birthday,usa,new york city,music,males,sean combs,andre harrell

4. Andre Harrell’s Birthday Party

Andre Harrell's Birthday Party Source:Getty

Naomi Campbell, Usher, Andre Harrell and Sean P. Diddy Combs (Photo by Johnny Nunez/WireImage) naomi campbell,arts culture and entertainment,horizontal,usa,new york city,males,females,sean combs,usher – singer,andre harrell

5. Sean P. Diddy Combs’ Surprise 35th Birthday Party

Sean P. Diddy Combs' Surprise 35th Birthday Party Source:Getty

Andre Harrell, Sean P.Diddy Combs and Kim Porter ***Exclusive*** (Photo by Johnny Nunez/WireImage) arts culture and entertainment,horizontal,usa,new york city,males,sean combs,exclusive,kim porter,andre harrell

6. Vote Or Die Political Art Exhibition

Vote Or Die Political Art Exhibition Source:Getty

Sean “P. Diddy” Combs, Andre Harrell and Don King (Photo by Johnny Nunez/WireImage) arts culture and entertainment,usa,new york city,males,sean combs,don king,andre harrell

7. Sean “Diddy” Combs “Press Play” CD Listening Party and Andre Harrell Birthday Party – September 25, 2006

Sean "Diddy" Combs "Press Play" CD Listening Party and Andre Harrell Birthday Party - September 25, 2006 Source:Getty

Andre Harrell and Sean “Diddy” Combs (Photo by Johnny Nunez/WireImage) arts culture and entertainment,usa,new york city,males,sean combs,andre harrell

8. Andre Harrell Celebration Dinner Hosted by Lyor Cohen

Andre Harrell Celebration Dinner Hosted by Lyor Cohen Source:Getty

NEW YORK – JANUARY 26: (L-R) Sean “P Diddy” Combs, Andre Jr. and Andre Harrell attend Andre Harrell’s celebration dinner hosted by Lyor Cohen at a Private Residence on January 26, 2009 in New York City. (Photo by Johnny Nunez/WireImage) celebrities,arts culture and entertainment,attending,horizontal,usa,celebration,new york city,males,sean combs,dinner,lyor cohen,andre harrell

9. Bad Boy Records Party for Carl Thomas – Hosted by Puff Daddy and Andre Harrell

Bad Boy Records Party for Carl Thomas - Hosted by Puff Daddy and Andre Harrell Source:Getty

Andre Harrell & Sean Puffy Combs during Bad Boy Records Party for Carl Thomas – Hosted by Puff Daddy and Andre Harrell at Atlas in Los Angeles, California, United States. (Photo by J. Vespa/WireImage) celebrities,arts culture and entertainment,horizontal,party – social event,usa,music,california,city of los angeles,males,father,sean combs,carl thomas,andre harrell

10. Sean “P. Diddy” Combs’ Surprise 35th Birthday Party

Sean "P. Diddy" Combs' Surprise 35th Birthday Party Source:Getty

Andre Harrell and Sean “P.Diddy” Combs during Sean “P. Diddy” Combs’ Surprise 35th Birthday Party at Figa in New York City, New York, United States. ***Exclusive*** (Photo by Johnny Nunez/WireImage) celebrities,people,arts culture and entertainment,horizontal,party – social event,birthday,usa,new york city,music,males,two people,sean combs,exclusive,andre harrell

11. Urban Aid Party

Urban Aid Party Source:Getty

NEW YORK – OCTOBER 5: Andre Harrell (L) and Sean ‘Diddy’ Combs (R) pose for a photo at a party after Lifebeat’s Urban Aid benefit concert at Madison Square Garden on October 5, 1995 in New York City, New York. (Photo by Catherine McGann/Getty Images) photography,celebrities,arts culture and entertainment,horizontal,party – social event,usa,new york city,looking at camera,waist up,portrait,music,concert,males,1990-1999,madison square garden,charity benefit,sean combs,lifebeat,benefit concert,andre harrell

12. Sean “P. Diddy” Combs Runs the City Pre-Marathon Dinner

Sean "P. Diddy" Combs Runs the City Pre-Marathon Dinner Source:Getty

Sean “P. Diddy” Combs and Andre Harrell during Sean “P. Diddy” Combs Runs the City Pre-Marathon Dinner at Metropolitan Pavilion in New York City, New York, United States. (Photo by Djamilla Rosa Cochran/WireImage) horizontal,usa,new york city,sport,males,city,track and field,sean combs,running,marathon,sports race,dinner,pavilion,track event,andre harrell

13. 21st Annual CFDA Awards

21st Annual CFDA Awards Source:Getty

Sean ‘P. Diddy’ Combs and Andre Harrell during 21st Annual CFDA Awards at NY Public Library in New York City, New York, United States. (Photo by Ron Galella/Ron Galella Collection via Getty Images) vertical,arts culture and entertainment,usa,new york city,males,cfda fashion awards,sean combs,council of fashion designers of america,andre harrell,public library

14. 2013 VMA After Party At PHD

2013 VMA After Party At PHD Source:Getty

NEW YORK, NY – AUGUST 25: Sean Combs and Andre Harrell attend the 2013 VMA After Party at PhD (Dream Downtown Hotel Rooftop) on August 25, 2013 in New York City. (Photo by Shareif Ziyadat/FilmMagic) celebrities,arts culture and entertainment,attending,horizontal,usa,new york city,males,after party,sean combs,andre harrell

15. Sean P. Diddy Combs’ Surprise 35th Birthday Party

Sean P. Diddy Combs' Surprise 35th Birthday Party Source:Getty

Andre Harrell and Sean P.Diddy Combs during Sean P. Diddy Combs’ Surprise 35th Birthday Party at Figa in New York City, New York, United States. ***Exclusive*** (Photo by Johnny Nunez/WireImage) people,arts culture and entertainment,horizontal,party – social event,birthday,usa,new york city,males,two people,sean combs,exclusive,andre harrell

16. 3rd Annual BET Honors – Show

3rd Annual BET Honors - Show Source:Getty

Andre Harrell (R) presents Sean P. Diddy Combs (L) with an award at the 3rd annual BET Honors at the Warner Theatre on January 16, 2010 in Washington, DC. (Photo by Johnny Nunez/WireImage) arts culture and entertainment,horizontal,usa,music,radio,television show,males,washington dc,award,annual event,black entertainment television,sean combs,bet awards,warner theater,andre harrell

17. Deleon Tequila Launch Party

Deleon Tequila Launch Party Source:Getty

NEW YORK, NY – NOVEMBER 20: (L-R) Andre Harrell and Sean ‘Diddy’ Combs attend Deleon Tequila Launch Party at Cedar Lake on November 20, 2014 in New York City. (Photo by Johnny Nunez/WireImage) arts culture and entertainment,attending,horizontal,usa,new york city,males,sean combs,cedar lake center,andre harrell

18. 2015 REVOLT Music Conference – Welcome Ceremony

2015 REVOLT Music Conference - Welcome Ceremony Source:Getty

MIAMI BEACH, FL – OCTOBER 15: Andre Harrell and Sean “Diddy” Combs attends 2015 REVOLT Music Conference Welcome Ceremony at Fontainebleau Miami Beach on October 15, 2015 in Miami Beach, Florida. (Photo by Aaron Davidson/Getty Images for REVOLT Music Conference) photography,celebrities,people,arts culture and entertainment,attending,horizontal,usa,music,males,two people,miami beach,gulf coast states,rebellion,three quarter length,ceremony,sean combs,fontainebleau resorts,2015,andre harrell,florida – us state,welcoming ceremony

19. Patrick McMullan Archives

Patrick McMullan Archives Source:Getty

NEW YORK CITY, NY – SEPTEMBER 11: Sean “P Diddy” Combs and Andre Harrell attend Heatherette Spring 2008 Collection at Gotham Hall on September 11, 2007 in New York City. (Photo by PAUL PORTER/Patrick McMullan via Getty Images) photography,arts culture and entertainment,attending,horizontal,usa,new york city,males,sean combs,gotham hall,andre harrell

20. Mary J. Blige Is Honored With A Star On The Hollywood Walk of Fame

Mary J. Blige Is Honored With A Star On The Hollywood Walk of Fame Source:Getty

HOLLYWOOD, CA – JANUARY 11: (L-R) Andre Harrell, Mary J. Blige, and Sean ‘Diddy’ Combs attend the ceremony honoring Mary J. Blige with a Star on The Hollywood Walk of Fame on on January 11, 2018 in Hollywood, California. (Photo by Rich Polk/Getty Images for Netflix) photography,celebrities,people,full length,arts culture and entertainment,attending,horizontal,usa,music,film industry,california,males,females,three people,fashion,hollywood – california,respect,ceremony,sean combs,mary j. blige,walk of fame,andre harrell

21. Andre Harrell Relaxes In A Nightclub

Andre Harrell Relaxes In A Nightclub Source:Getty
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