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Jadakiss is an iconic New York hip-hop artist who made his name as part of the hip-hop group The LOX. Comprised of Jadakiss, Sheek Louch, and Styles P, The LOX had great success in the late 1990s and early 2000s, and its members also received critical acclaim as solo artists.

However, before he pursued a solo career in the 2000s, Jadakiss and his crewmates were signed to Diddy’s Bad Boy Entertainment. The collective released music through the label but also worked behind the scenes. Akin to Ma$e, before their stardom they wrote a lot of songs for Junior M.A.F.I.A, Diddy (then known as Puff Daddy) and Biggie Smalls.

Unfortunately, The LOX had a tough time while signed to Bad Boy as their rough and rugged style of writing lyrics didn’t fit well with the label’s luxurious, opulent rhymes. Diddy, Lil Kim, and other acts on the label projected a lavish lifestyle, and this mainstream desire at the time was epitomised by a lot of the music Biggie Smalls released.

That said, while writing for Bad Boy, Jadakiss teamed up with Biggie for the track ‘Last Day,’ which appeared on his 1997 album Life After Death. However, the initial rhymes written by the Yonkers emcee were rejected by Biggie Smalls, who rudely told him to throw them in the trash and start again.

This was Jadakiss’ big break as an artist and was the first time he had been asked by Diddy to appear alongside Biggie Smalls on a track. Still, Jadakiss’ style wasn’t for purpose in the eyes of the late Brooklyn icon.

In a 2003 interview with XXL magazine, Jadakiss recalled working on ‘Last day’ with Biggie and vividly depicted it, explaining, “When we did ‘Last Days,’ we were still, I wouldn’t say rookies, but we were new to the Bad Boy family. “We got the call from Darren [Joaquin Waah Dean] from Ruff Ryders, our manager back then. He wanted us to go to Daddy’s House. We didn’t even know we was getting on a B.I.G. album, so when he called us to get on it, we was wild happy.”

Recounting his happiness and excitement at the time, Jadakiss continued, “We go down there, walk in, and it’s smoky — they used to have it like the Shaolin Temple. Anyway, the beat’s knocking, Junior M.A.F.I.A. was in there, and we was drinking, smoking heavy, living the dream, like, ‘We about to get on a song with Big!’”

According to the ‘Get That Paper’ rhymer, Biggie was in charge of the final product regarding rhymes, and although his rejection sounded harsh at the time, it made him want to write better lyrics.

Recalling his initial interaction with the Ready To Die legend, Jadakiss told XXL, “I had a verse I wanted to use, something that I had already. I was probably being lazy. I spit it to Big, and he was like, ‘Nah, Kiss, I know you can come harder than that. Don’t use that one, make something right now.’ I was like, ‘Damn, Big told me to do it over. I know I got to come with another one.’ So I came with the joint I came with, and he was just feeling that s*** crazy.”

Biggie Smalls loved the second verse, and it made it on the final edition of Life After Death, which was released after the rapper’s tragic 1997 murder.