Kris Kaylin brought some of South Carolina’s rising stars to Charleston for the first-ever Princess Diaries Live show.

Headliners Lil Boss, Trap Dickey, and Juhovah at Princess Diaries Live. Photo by Jovon Roberts

Media personality and culture curator Kris Kaylin — better known as the Princess of Charleston — isn’t just building her throne in the media; she’s inviting the voices of the Carolinas to join her. Her podcast, Princess Diaries — known for its unfiltered takes on love, hustle, and life’s intricacies — became a full experience this past Thursday with its first-ever live event. With a twice sold-out crowd, a live band, and a lineup featuring South Carolina’s rising artists like Trap Dickey, Lil Boss, and Juhovah, the vibe was certified before the show even began.

Before things officially kicked off, Kris’s mom, Ms. Roberta opened the night with a heartfelt introduction, lifting up her daughter’s journey and emphasizing the importance of nights like these. Bossalinie Breezo hit the stage first, backed by the live band, bringing the Geechie sound to the forefront. He performed his single “Trust” along with a few unreleased tracks.

Dressed in all pink, Kris Kaylin then graced the stage for the first time that night. Heavy cheers and shouts filled the room. You could feel how intense the support was. Trying to hold back tears, she thanked everyone for showing up and jumped right in, introducing the first interview with Juhovah.

Kris Kaylin takes it all in at the first-ever Princess Diaries Live event. Photo by Ricardo Rivers photography

R&B heartthrob Juhovah, from Florence, SC, joined Kris on stage. For those who only knew him as a ladies’ man through his music, this was the perfect intro. He shared his journey of moving around a lot as a kid, attending almost every high school in Columbia before eventually making his way to Atlanta, where he started making music. Ironically, his first song was a track he made to express his feelings to a girl. His career since then has been “trial and error,” choosing the hard route by doing things his way, but with no regrets.

And undoubtedly so, as Juhovah has seen major success: his hit “Soft Girl Era (feat. Geovarn & Ling Hussle)” has over 2.3 million streams, and he’s attended the BET Awards the last two years. The first time, he had no invite, ticket, or credentials — just determination. After standing in the LA heat, fully suited for two hours, he managed to walk the red carpet, just like he said he would.

Not stopping at music, Juhovah is now expanding into talent management. When Kris asked if he thought that could be a conflict, he laughed, “Guess we’re about to find out,” before emphasizing, “there’s more than enough room for everybody” and “there’s no limit on blessings.”

Next up was Charleston’s Priscilla Simone, whose rich, soulful voice barely needed a mic. Backed by the live band, she performed “Little Moon” and an unreleased track with Khandee Brown.

Kris brought out Charleston’s own Lil Boss to join her for the next interview. His city anthem “Topic” got the world’s attention two years ago, but that night, it was his confidence and authenticity that captivated the crowd. When Kris asked how he would describe Charleston’s sound, he didn’t hesitate: “Geechie.” He added that he has his own dialect and doesn’t think he sounds like anybody else. When asked to name his Mt. Rushmore of rap, his answer was just as audacious: “All me. I don’t want to put nobody in front of me.”

While his energy was infectious and had the crowd laughing the entire time, his genuineness stood out the most. Taking care of his people, he made clear, is his main goal and motivation. That, mixed with his love for music — honed freestyling at family reunions as a kid — keeps him going.

New music is on the way soon, he assured, and when it’s time there will be no mistaking it — you will see him coming.

Lil Boss shares the stage with Kris Kaylin — a full-circle moment. Photo by Ricardo Rivers photography

Tommy Brown, also repping Charleston, who was next to rock the stage, delivered one of the most engaging performances of the night. He had the crowd singing along to his song “Like Water”, teaching everyone the words mid-performance. With a voice strong enough to stand on its own, he still made sure to pause and give the band their spotlight.

Wrapping up the interviews for the night was Trap Dickey from Hartsville, SC. The moment Kris called him on stage, the room erupted with applause and shouts of “Traaappp!”— a true showcase of Carolina love and support.

With co-signs from big names like DaBaby, OJ da Juiceman, and BigXthaPlug, Trap knows he’s playing in the big leagues now, but has no plans to change who he is. His success has already taken him far — this year, he sat front row, alongside Juhovah, at the BET Awards right next to SZA — proof of Carolina’s growing reach. His breakthrough hit “Blue Devils” continues to build momentum, and we can soon expect an EP or mixtape from him before the album drops.

When it comes to dream collaborations, Trap’s aiming high: Andre 3000, Big Boi, T.I. — “anybody who ever claimed to be the King of the South.”

But more than just the music, Trap spoke about giving back to the community — showing kids they don’t have to take the same route he did and advocating for stricter gun laws to keep the youth safe. As he put it, “Success [is] supposed to change the people around you,” and for him, that means creating opportunities for all of the Carolinas to grow and shine. Because, as he reminded everyone before leaving the stage, the South still got something to say.

Closing out the night was Charleston’s LUVHUTCH, performing his catchy single “Dinner”, a hook you couldn’t help but sing along to. He brought out Bluflame James to perform their song “Champagne Hotbox,” and the two freestyled mid-song, the perfect vibe to end a night that was already on a high note.

LuvHutch and Bluflame James backstage at Princess Diaries Live. Photo by Ricardo Rivers photography

And just like that, the first-ever Princess Diaries live show was wrapped. From pink decorations, gift bags, and wristbands to the branded cups and outfit changes, every detail throughout the night screamed “Princess Treatment” as Kris likes to say. DJ Shae Balboa kept the energy live all night, turning the room into a party in between each set. The night was both a conversation and celebration of South Carolina’s recent and well-deserved spotlight. Kris Kaylin proved the Carolinas aren’t just here to watch the throne, they’re building their own.

Relive the night by checking out the Princess Diaries Podcast and the Certified Vibe x Princess Diaries playlist curated for the event!