The passing of publishing icon and celebrated ladies' man Hugh Hefner rocked the world of entertainment last week, with many celebrities mourning the world's loss of a man who truly changed the pop culture landscape forever. Pamela Anderson shared a tearful farewell via Instagram, and others such as 50 Cent, Diddy and Juicy J all offered up their most heartfelt messages to Hef, who was 91. However, one of the more surprising tributes in the wake of his death was from Lil Kim, who revealed that she has a singular regret when it comes to Hefner and the legacy of Playboy: turning down the opportunity to work with them.

"This is one man that I thought would live forever," she began, captioning a picture on her Instagram page of her and Hef exchanging a small kiss during a ritzy event for the Bunny brand. "Ugh I'm so broken-hearted that I didn't get to spend more time with him 😞 Hugh believed in my beauty more than myself, he always put me on a pedestal." Kim went on to extol the positive qualities of a man who few people got to know past his public persona.

This is one man that I thought would live forever. Ugh I'm so broken-hearted that I didn't get to spend more time with him 😞 Hugh believed in my beauty more than myself, he always put me on a pedestal. If you got to know him it was a pleasure and honor. He was such a great wonderful spirit and so much fun! I remember turning down a non-disclosed 7 figure offer from Hugh and till this day I regret it, not because of the money, but because it would have been an honor to be a part of this beautiful mans archive and historic catalog. You never changed up and you were always the same kind loving person. Every time I saw you, even after the fact that we didn't get to make history 2gether, our love for each other always remained the same. I Love You to the heavens Hugh and I will miss you dearly 💔 #riphughhefner

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"If you got to know him it was a pleasure and honor. He was such a great wonderful spirit and so much fun," she continued. Then came the bombshell: one of rap's original queens turned down a hefty payday that Playboy offered her back in the day. "I remember turning down a non-disclosed 7 figure offer from Hugh and till this day I regret it, not because of the money, but because it would have been an honor to be a part of this beautiful mans archive and historic catalog." There's no telling what exactly she would've been asked to do or how to pose, but for that kind of money, it's hard not to sympathize with Kim's wish that she could have a do-over with that decision. "Every time I saw you," she said of Hef, "even after the fact that we didn't get to make history 2gether, our love for each other always remained the same.  I Love You to the heavens Hugh and I will miss you dearly."