[Photos] Legend Conversation: Little Brother

On 9/12/25 we hosted Legend Conversation: 14 featuring Rapper Big Pooh and Phonte of Little Brother. The night featured delicious food from Chef David Silva of Dope Drip Cafe, as well as drinks from Tito’s Handmade Vodka, Johnnie Walker, and Moors Beer.

For the merch item, we decide to do our first straight up Legend Conversation Tee, with an inside nod to the way in which Little Brother got their name. According to their documentary, they were experimenting with various options and decided to sketch out a concert lineup featuring A Tribe Called Quest, Slum Village, The Roots, and…. The … would become their name. They said Little Brother just felt right. For the tee, we listed all of the artists that have participated in Legend Conversation to date, with Little Brother appearing at the bottom, as the most recent. Imagine if that t-shirt was festival!

After dinner and drinks, Pooh and Phonte sat down with DJ RTC and Dave Jeff to talk about their experiences in and out of Little Brother, what “retirement” means to them, and how they repaired their relationship to put a proper closure on Little Brother.

See photos below from Pedro Ramirez. If you see yourself, grab it, post it on social media and tag us @legendconversation.

Our next Legend Conversation happens 11/14. Join our mailing list for a chance to attend.