R&B powerhouse Leela James and rising artist Connie Diiamond joined Angela Yee’s Lip Service podcast for an open and engaging conversation on music, relationships, and authenticity. The two discussed the drastic evolution of the industry, the balance between fame and privacy, and what it takes to remain grounded in a business that often demands constant reinvention.
James, who made her debut in 2005, reflected on how much the industry has transformed over the past two decades. She noted how shorter attention spans and an oversaturated market have made it increasingly difficult for artists to stand out. Where the early 2000s produced distinct voices like D’Angelo, Jill Scott, and Erykah Badu, today’s digital era is dominated by algorithms, viral moments, and a nonstop demand for content. Both artists acknowledged that social media has opened doors for connection but blurred boundaries between artistry and personal exposure, erasing much of the mystique that once defined celebrity culture.
James also shared her brief stint on reality television, explaining how what began as an exciting opportunity on R&B Divas quickly turned into an uncomfortable experience. She found that much of reality TV lacked authenticity, with producers staging drama for entertainment. The experience reinforced her desire to protect her personal life, especially as a mother. After taking a four-year hiatus from music to focus on her family, she returned with a renewed perspective on what balance looks like for women in entertainment, acknowledging the physical and emotional weight of motherhood while maintaining a career.
For Diiamond, who recently released Underdog Season 2, vulnerability has become a central theme in her music. Her latest project opens with an honest letter to herself, highlighting the challenges of navigating the industry without sugarcoating the realities behind the grind. She wants fans to experience her journey in real time rather than through polished, post-success interviews.
The pair also spoke about the loss of organic collaboration in today’s music scene. They reminisced about earlier eras when artists gathered in studios and shared creative energy, contrasting it with today’s remote, file-sharing culture. Both agreed that physical presence and shared space often bring out the best in artistry. Location continues to play a role in their creativity, Diiamond draws inspiration from traveling and recording in new environments, while James often returns to her California roots for inspiration, drawn to the beaches and atmosphere that remind her of home.
When the conversation turned to relationships, James reflected on lessons from her first marriage and how taking time between relationships helped her rediscover herself. Now remarried, she values emotional maturity and timing, believing her current marriage thrives because both partners grew individually before coming together. Diiamond, who’s been in a relationship for over a year, described herself as openly affectionate and grateful for a partner who understands her demanding career and doesn’t react with jealousy or insecurity.
The discussion expanded to gender dynamics and financial independence. James emphasized the importance of maintaining individuality and personal space in relationships, even down to keeping separate closets. She spoke about the value of financial autonomy and the need for women to preserve independence, a lesson she learned through experience. While both artists advocate for women’s independence, they agreed that men should still contribute financially, seeing it as a matter of respect and balance rather than dependence.
The group also touched on public judgment and past experiences. James and Diiamond both rejected the idea of being defined by their pasts, embracing their growth and evolution. James reflected on her journey from working retail to achieving longevity in music, while Diiamond admitted that she’s her own biggest critic but focuses on progress rather than perception.
Host Gigi added to the conversation, sharing her own path from exotic dancing to documentary filmmaking, highlighting how owning one’s story can transform past challenges into empowerment.
On the creative side, Diiamond revealed her recent struggles with perfectionism and the pressure to maintain her image as a lyricist. While working on a freestyle over a Cardi B track, she admitted losing some spontaneity but remained determined to present her work as effortless despite the hard work behind it. James echoed the importance of authenticity in music, emphasizing that the soul can’t be manufactured, it must come from a place of truth and feeling.
Both artists laughed about misconceptions surrounding record deals, pointing out that signing to a label doesn’t guarantee financial comfort. James recalled being signed to Warner Brothers and still struggling financially, while Diiamond agreed that even signed artists often operate like independents, handling their own promotions and projects.
As 2025 approaches, both artists are closing out the year with gratitude and focus. James is wrapping up a few shows before taking time off for the holidays and heading to Europe in January. While touring has become more of a balancing act as a mother, she remains thankful to perform. Diiamond, entering her first holiday season living alone, admitted to feeling anxious about the industry’s end-of-year slowdown but was encouraged by James and the hosts to embrace it as a creative reset.
Both women ended the conversation by celebrating their growth, artistry, and resilience. Leela James continues to honor her legacy as one of R&B’s most consistent voices, while Connie Diiamond steps into her prime, proving that talent, authenticity, and perseverance remain the true keys to longevity in music.
