Jay-Z Disses Damon Dash in Freestyle Rap – Dash Responds

Jay-Z had nothing but insults for Damon Dash over the weekend at the 2026 Roots Picnic in Philadelphia.

After taking the stage on Saturday, the “99 Problems” rapper unloaded on his enemies and rivals, including Roc-A-Fella Records co-founder Dash.

Jay-Z began by belting out his 2002 hit “Hovi Baby” and he let the insults fly.

Videos posted by Roc Nation and attendees on social media, showed the rap mogul taking a string of verbal jabs at Dash, who recently filed for bankruptcy amid a string of financial troubles.

“Another fumbling, he’s wondering how I get the blame/Ni–as teeth is tumbling out they mouth and somehow I’m the one who done it/It’s a murder mystery gang,” Jay-Z rapped.

While he didn’t say Dash’s name, it was pretty clear the fumbling [the bag] line was in reference to the entrepreneur’s financial issues.

As for the teeth “tumbling out,” that happened to Dash during a livestream with fans in September 2024. After taking a sip from a glass, his false teeth slipped out of his mouth, prompting Dash to say “Oh s–t!”

Dash seemingly responded to Jay-Z’s insults with a diss of his own. On Sunday, he posted an AI-generated image on Instagram of Disney character “Goofy” dressed in an outfit similar to the one Jay-Z wore on stage. Dash tagged his former business partner in the post and included a laughing emoji.

The rapper, born Shawn Carter, and Dash
co-founded Roc-A-Fella Records with Kareem “Biggs” Burke in 1994. But Jay-Z and Dame’s relationship soured years ago.

Dash has criticized him multiple times in interviews. So, on Saturday the “Excuse Me Miss” rapper responded.

Jay-Z also took shots at attorney Tony Buzbee, Kanye “Ye” West, Nicki Minaj, Drake, Tony Lanez, and Jaguar Wright in his freestyle.

Roots Picnic is an annual music and culture festival created by the legendary Philadelphia hip-hop group The Roots. Each year the festival draws thousands of fans.

Check out Jay-Z’s rap above and Dash’s response below.