If you ever sit down with hip hop legends, you’ll hear them share stories of what they consider to be their biggest L’s. Missed opportunities seem to be what can plague an artist, and in a recent chat with the No Filter Podcast, Erick Sermon had no problem sharing two regrettable decisions that he lives with until this day. 

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Christopher “Notorious B.I.G.” Wallace is hailed as one of the best rappers to have ever picked up a mic, although his career was short-lived. The 24-year-old rapper was gunned down in Los Angeles during a drive-by in 1997, and by that time he was already a hitmaking, award-winning star. However, before he became the big-name rapper that we know today, he was just Biggie from Brooklyn trying to make it in the industry.

Erick shared that he had run into Biggie around New York and expressed interest in working with the rising rapper. When Biggie heard that Erick was working on a record, he sent word to the hip hop icon that he wanted to a spot on the album. Erick now shares that he turned Biggie down and told him no because he had his own crew including the likes of Redman and Keith Murray, and admitted that he didn’t think featuring B.I.G. would be a good fit.

Sermon also shared that he turned down an opportunity to work with Nas a producer on his critically-acclaimed classic album Illmatic. “So he comes and sits down, I give him C-list beats Doggy. Because don’t forget all my rappers is ‘Wiggity Wow’ and when I ‘S-P-E-L-L’ and I got Redman, I have these others. So that street content, I couldn’t really get with that. I know it sounds crazy, though, man.” He added, “I didn’t hear Illmatic, he was making Illmatic. When he left me, he went to Pete Rock... I’m sitting here thinking that this is a kid from Queens that is just rhymin’ again, but I don’t understand.”

Nas and Sermon did end up working together and according to Sermon, they completed three songs. However, the studio that housed the tracks burned down. Meanwhile, after Illmatic came out, Erick said he wasn’t immediately regretful. “I’m ain’t gon’ lie to you, I didn’t look at it like that at that time then. I was a star,” he said. “Business As Usual was out and now we getting ready to drop ‘Crossover’ and ‘Headbanger’ and I got Redman coming out. Don’t forget, that wasn’t my style of rap.” Check out Erick Sermon share his stories below.