This week’s episode of Highstreet features rapper Hundredround Kado, frequent collaborator Lazy Coca, and comedian Owen from King’s Court Stand Up, joining the hosts for a conversation that blends music, comedy, and personal reflection.
As is tradition, the episode opened with a new world premiere track and closed with a lighthearted round of the podcast’s signature game Highball.
Kado discussed working with producer/engineer Dallas on multiple projects, while also reflecting on a diss track that reached 400,000 views and involved Baltimore artists and DDG. The conversation touched on recording techniques, weighing the energy of analog approaches against the convenience of digital, and the importance of capturing authentic performances.
Owen, who runs cannabis-themed comedy shows in Cambridge at Diaspora, spoke about the challenges of performing in an era shaped by social media. The group reflected on how audiences, often overstimulated and used to short-form content, consume art differently compared to live performance experiences. The vulnerability of stand-up comedy was a recurring theme, described as one of the rawest art forms that requires taking risks in front of an audience.
A significant portion of the episode centered on mentorship and transformation. Kado described stepping back from his own pursuits to support younger artists, comedians, and streamers, often hosting them in his home. He emphasized the importance of letting go of past expectations, or “mourning” former ambitions, to find meaning in helping others succeed. The discussion also included experiences with psychedelics, ego death, and personal healing.
The episode highlighted Baltimore’s creative community, including stories about emerging talent like Lil Reggie. Kado reflected on making amends with people he had once bullied in school and building genuine friendships through humor and honesty. The conversation stressed the importance of laughter as a tool for connection and healing.
The group exchanged perspectives on authenticity, emphasizing that people should not try to change others but instead allow them to be themselves. They spoke about responsibility, humor, and the balance between not taking life too seriously while remaining accountable. Conversations also touched on hip-hop legacy, referencing artists like Nas, Jay-Z, and 50 Cent, and discussing the difference between timeless music and fleeting viral moments.
The episode wrapped with the hosts and guests playing Highball, followed by a freestyle verse that reflected on street life experiences, underscoring the episode’s blend of raw storytelling, philosophy, and lighthearted camaraderie.
