No. 28: Pharoahe Monch

Troy Donald Jamerson would have had a shot at making the top 50 based on his work with Organized Konfusion alone. He also would have been a top-50 lock based on his solo career alone.

Combine the two, and it almost seems unfair that Pharoahe Monch is ranked this low.

Maintain the same frame of mind...screw ya.

Organized Konfusion became an underground favorite with its three acclaimed albums during the mid-1990s, with Monch and Prince Poetry delivering complex rhymes over beats produced largely by themselves. When props and respect didn't translate into sales, the group split, and Pharoahe began his solo career by signing with Rawkus Records.

His debut LP, 1999's Internal Affairs, proved to be one of the better overall records of the late 1990s. Fueled by the lead single, "Simon Says," the album showcased Pharoahe's skills on such tracks as "Queens," "The Ass" and "The Light." Even on "Simon Says," where the hook screams crossover attempt, the rhymes were still on point:

Some might even say the song is sexist-est/'cause I ask the girls to rub on their breastices
Whether you're riding the train or in Lexuses/this is for either or Rolies or Timexeses
Wicked like exorcists shit this is the joint/you holding up the wall then you're missing the point...

Monch also made countless notable guest appearances around the same time, appearing on Rawkus' Soundbombing II as well as Sway & Tech's "The Anthem." He shone particularly brightly on a 2000 collaboration with Mos Def and Nate Dogg, "Oh No":

Pharoahe and Mos we verbalize most/coast to coast, we boast to be the most explosive here
Ferocious, the lyrical prognosis, the dosage is leavin' you mentally unfocused here...

After a few years of laying low, Monch quietly released his second and third solo albums in 2007 and 2011. While commercial success has continued to elude him, he remains — and rightfully so — one of the most respected emcees in hip-hop history.