Questlove has “second thoughts” about appearing on Jay-Z’s Unplugged album, which included a live performance of Hova’s infamous Nas diss track, “Takeover.”

The Roots drummer has been under fire for his controversial takes on the Kendrick Lamar vs. Drake feud and his recent take on Tupac’s classic diss track, “Hit ‘Em Up.” After saying “Hip hop truly is dead” in response to rap fans debating over who won the lyrical war between Kendrick and Drake, critics reminded Questlove about his role in one of the most high-profile rap beefs of all time.

It was 2001 when Questlove, 53, played the drums on Jay-Z’s live Unplugged album where the hip-hop mogul performed his scathing “Takeover” diss during the height of his rap feud with Nas. Looking back on the performance, Questlove has some regrets.

“& yeah you don’t have to remind me of my role on Unplugged——-that wasn’t one of my brighter moments & had I had a redo I prolly woulda had second thoughts of the “Takeover” situation,” he wrote in a lengthy Instagram caption addressing the backlash.

“I mean I know I’m old y’all but damn I’m not tryna be #Poundcake/Respectable Politics Smurf over here yelling “Get Off My Lawn!!!” every 14 secs.”

Elsewhere in the post, Questlove responded to negative responses he received after calling Tupac’s “Hit ‘Em Up” the “weakest musical smack” in rap beef history.

“I would actually respect 2Pac’s ‘Hit ‘Em Up’ if his music tracking was better,” he said on SiriumXM’s One Song podcast last week. “‘Hit ‘Em Up,’ to me, is disqualified not because of the misogynist…Dude, you’re rhyming over smooth jazz dinner music! Luther Vandross could sing over this!”

He continued. “So when this came out, everybody was like, ‘This is hard as sh–! Yo, he killin’ it!’ And I was like, ‘Dog, he’s smooth jazzed up Dennis Edwards. It doesn’t count.’…That song, to me, is the weakest musical smack. I can’t get with ‘Hit ‘Em Up.’”

Journalist Elliot Wilson took to X to call out Questlove for the controversial take.

Yo! Questlove we love you, but you gotta stop. pic.twitter.com/ztMM468Lnp

— Elliott Wilson (@ElliottWilson) May 14, 2024

When responding to all the backlash from the public on Tuesday, May 14, Questlove made sure to tag Wilson to his response about the Kendrick-Drake feud, Tupac’s “Hit ‘Em Up,” and his appearance on Jay-Z’s Unplugged.

“Let’s be clear on the context I was speaking of aight? lol woke up to a grip of ‘what did Dennis Edwards/Pac do to you?!’ texts I’m speaking of the musical backdrop of that record (“Hit Em Up”),” Questlove wrote in his caption.

“Still mostly not a fan of dis records mostly because having lived in that period (mid 90s) I never seen any good results from hip hop beef.”

RELATED CONTENT: Questlove’s New Book ‘Hip-Hop Is History’ Coming June 2024