Isaiah Rashad picks the “most entertaining” rapper
Tennessee emcee Isaiah Rashad is an artist who arguably doesn’t get the recognition he deserves. The Top Dawg Entertainment (TDE) act has been releasing music for years, and with projects such as The Sun’s Tirade and Cilvia Demo showcasing the best of hip-hop, it is sometimes difficult to understand why the lyricist hasn’t achieved as much success as his TDE counterparts SZA, ScHoolboy Q and Jay Rock.
Rashad has been a mainstay in the culture since the early 2010s and has worked with a range of well-known artists, including Lil Uzi Vert, Smino and Juicy J. However, he still hasn’t been able to break into the mainstream.
Irrespective of his current status as an artist, Isaiah Rashad has been recognised by all the greats. As such, it was unsurprising when, in 2021, following the release of his sophomore album, The House Is Burning, the Chattanooga rhymer appeared on Talib Kweli’s People’s Party podcast to speak about some of the most entertaining rappers of all time.
As the two lyricists sat down, Rashad began by speaking about Louisiana legend Lil Wayne. During their conversation, the 33-year-old suggested that Wayne could possibly hold the title of “The Most Entertaining” hip-hop artist of all time.
Delving into why he thinks the Young Money founder may have that crown, Rashad explained, “So Lil Wayne’s leaks from Tha Carter III were kinda crazy, and he had some of the more passionate shit out of [the] Cash Money [artists].” He continued, “For example, some of the song’s from his first album talking about his dad and shit and when his step-dad died. So that n*gga was really an archetype ‘cause he really was to me the most entertaining rapper ever.”
Although he believes Wayne is the most entertaining, he expressed that he doesn’t think he is the best rapper of all time and handed that title to Jay-Z. As he humorously praised Hov, Rashad added, “I guess Wayne couldn’t be the best ‘cause you can’t be better than Jay-Z!”
However, showing his love for Southern music again, he also named Young Thug as a contender, exclaiming, “Thug’s amazing. He up there. I think he’s trying to take Wayne’s spot for the most entertaining rapper ever ‘cause that n*gga hard!”
Another Atlanta emcee Rashad put forward as a potential winner was Ludacris, although there was a bit of hesitancy. Floating the idea, he told Kweli, “Ludacris is top five commercially. He’s a top-five entertainer. It seems like Hollywood took his rap ability out to be able to release movies.”
Kweli insisted “there is a case to be made” concerning Ludacris but still wasn’t entirely convinced that he could be close to number one in any way. Isaiah and Talib had a lengthy discussion about hip-hop and how it has evolved in recent times, and Rashad’s perspective as a new-school Tennessee-based lyricist was intriguing to Kweli.