On Wednesday (Sept. 27), Playboy founder Hugh Hefner passed away at the age of 91. With his unflappable cool, undeniable vision and his way with the ladies, Hefner became one of America's most iconic tastemakers—and someone hip-hop luminaries could also admire. Especially since he seemingly always showed love.

Within hours of Hef's passing, everyone from French Montana to DJ Premier to The Weeknd to Diddy paid tribute to Hefner's passing. "Rest in peace to my man Hugh Hefner!! Love You, Puff! You will be missed!!!" said the Bad Boy mogul in an Instagram post including an image of Hef rocking his signature sailor's hat.

When they didn't include images of just Hef, they posted pictures of the legend surrounded by women from around the time Playboy was hitting its stride to the 2010s. No matter what decade it was, Hef was clearly winning. It's no wonder French called him someone he looked up to.

"WOW !! Rip to my one of my idols 🙏 Hugh m. Hefner😢 life is short enjoy it 🙏," French wrote in an Instagram post with an image of Hef standing in front of California's famous Hollywood sign. No matter what Hef ever seemed to be doing, there were rarely ever awkward moments with the guy, as he personified coolness as he made moves with ambition of a visionary.

Today, XXL takes a look at what members of the hip-hop community have to say about his passing. Check out what they have to say in the gallery of tweets below, and after that peep the images rappers and producers threw up on IG.

See How Hip-Hop Reacted to Playboy Founder Hugh Hefner's Death