For Jessie Berg, 21, the decision to pivot from traditional academics to a full-time pursuit of her music career was not made lightly, but it is one she absolutely stands by. With no regrets, she recounts how her artistic journey began early in Los Angeles, immersing herself in various creative outlets. “I did plays [and] I did choir type [of] stuff,” Jessie revealed to HollywoodLife EXCLUSIVELY while discussing her captivating new single, “Know Me.” These formative experiences, from the spotlight of local theatrical productions to the harmonies of choral groups, laid a robust foundation for her burgeoning musical aspirations. Her childhood also included dedicated voice lessons at a local studio, culminating in regular performances at their community showcases. These early stages were crucial for developing her vocal technique, stage presence, and an innate understanding of performance art. However, it was after high school graduation that her ambition truly ignited. With more time and newfound independence, Jessie was able to channel her energy entirely into creating her own music. This period saw her working diligently at her cousin’s studio, learning the intricacies of recording and production firsthand. While she briefly enrolled at Santa Monica College, attending for only a single semester, her heart remained firmly rooted in her musical endeavors. The pull of her true calling proved too strong to ignore. “I just stopped going. I never told them, I just never showed up again,” she admits, a testament to her resolute commitment to her artistic dreams, choosing the unpredictable but exhilarating path of an independent musician over a conventional academic route.

This bold decision to fully commit to her craft was significantly shaped by the professional guidance of her seasoned manager, Kent Jacobs. With an impressive resume that includes working with legendary acts such as REM, Drake, 32, The Police, and Prince, Jacobs brought a wealth of industry experience and strategic vision to Jessie’s career. Under his mentorship, Jessie was empowered to dive deeper into her artistic identity, exploring and refining her unique sound, vocal range, and creative inspirations. This period of intense self-discovery allowed her to move beyond merely performing to truly crafting her narrative through song. Jessie describes her songwriting process as profoundly intuitive and organic. “I never really had a plan of what I want to say in a song,” she explained. “I feel like if I plan stuff, it doesn’t work out so I just show up and whatever I think of, that’s it. The way I write music is very in the moment.” This spontaneous approach allows her to capture raw emotions and immediate thoughts, lending an authentic and relatable quality to her lyrics and melodies. It’s a method that prioritizes genuine expression over preconceived notions, ensuring that each track reflects a true fragment of her experience and perspective as a rapidly evolving pop artist.

While Jessie Berg holds ambitious aspirations of collaborating with global music icons such as Rihanna and Kanye West someday, she has already achieved remarkable success in forging partnerships with respected talents within the industry. To cultivate her distinctive “left of center pop” sound, Jessie has teamed up with renowned names like The Aristocrats, Pierre Lupinani, and Brian Kennedy. These collaborations have been instrumental in shaping her unique sonic identity, blending unexpected elements into a fresh, accessible pop framework that defies easy categorization. Her “left of center pop” vibe is characterized by its innovative production, emotionally resonant lyrics, and a willingness to experiment with genre boundaries, setting her apart in the contemporary music landscape. But beyond her professional collaborations, there’s one dream duet that holds a special place: a potential collaboration with her dearest friend, Ariel Winter, 21. “I’d be down,” Jessie enthusiastically stated, expressing her eagerness for such a project. “I would probably do it, but I don’t know if she wants to do anything singing related. I know she was focusing on acting, but I’ve talked about it with her.” The idea of combining their creative energies, even if Ariel’s primary focus is acting, highlights the deep bond and mutual respect that defines their friendship. Such a collaboration would not only be a treat for fans but also a celebration of their enduring connection, blending their individual artistic strengths into something truly unique and memorable.

Despite having an accomplished team of respectful producers and a seasoned manager backing her burgeoning career, Jessie Berg consistently values and readily accepts advice from her famous best friend, Ariel Winter. Their bond, forged since freshman year of high school, has provided Jessie with a unique vantage point into the demanding world of entertainment. “I feel like Ariel has given me so much advice,” Jessie revealed, highlighting the depth of their shared experiences. “I’ve literally seen everything because we’ve been best friends since freshman year of high school, so I’ve seen a lot and I’ve just learned a lot from her, watching her do everything she’s done in her career and everything.” This intimate perspective has offered Jessie invaluable lessons on navigating fame, maintaining authenticity, and enduring the pressures of public life. Ariel’s relentless work ethic and unwavering pursuit of her goals have been a powerful source of inspiration. “I talked about it before that seeing somebody who works that hard and goes after what they want day after day after day, and is able to go through what she’s gone through and still come out as incredible as a person as she is, it makes me want to work harder,” Jessie passionately explained. Furthermore, Ariel has instilled in Jessie a crucial lesson about self-acceptance and resilience. “She’s the type of person that doesn’t care about what other people think, and so she’s passed that on to me as well, and I’ve become more of a, I don’t want to say extrovert, because I’m not an extrovert, but just I’ve become more myself. I’m more comfortable and secure in myself, and I just am not as scared as I used to be.” This profound influence has allowed Jessie to shed insecurities, embrace her authentic self, and approach her career with newfound confidence and self-assurance, a testament to the powerful impact of genuine friendship and mentorship in the competitive entertainment landscape.

The profound impact of Ariel Winter on Jessie Berg’s life and career is evident, and the admiration is clearly mutual. Ariel, who has recently been in the spotlight herself with reports of her breakup with longtime boyfriend Levi Madden, 32, expresses immense pride and happiness for her friend’s impressive journey and accomplishments thus far. This genuine support underscores the strength of their enduring friendship, a bond that transcends the typical complexities of the entertainment industry. Jessie often reflects on Ariel’s unique experiences and resilience. “I think about it a lot, honestly,” Jessie revealed. “Her life is crazy and everything she’s been through is more than I think any person should have to, and I think people think that she is such a giving and caring and just genuine person. She’s doing really well.” This insight from Jessie highlights not only Ariel’s ability to navigate an extraordinary life but also her remarkable character, marked by generosity, compassion, and authenticity despite facing numerous public challenges. Ariel’s journey, often under intense scrutiny, has paradoxically empowered Jessie to be more fearless and grounded in her own artistic pursuits. It’s a relationship built on mutual respect, admiration, and a shared understanding of the highs and lows of a life lived in the public eye. This foundation of support allows both women to thrive, each celebrating the other’s successes and offering solace during challenges, making their bond a powerful force in their respective careers.

As Jessie Berg continues to captivate audiences with her evolving sound and genuine artistry, fans have a thrilling opportunity to experience her latest work. Be sure to check out Jessie’s newest single, “Monster,” which is available now across all major platforms. This track is a powerful testament to her “left of center pop” style, showcasing her distinctive vocals and profound songwriting capabilities. “Monster” delves into themes that resonate deeply, offering a glimpse into Jessie’s artistic growth and her ability to craft emotionally compelling narratives. But the excitement doesn’t stop there. Jessie has confirmed that even more new music is slated to drop in January 2020. This upcoming release promises to further solidify her position as an artist to watch, delivering fresh sounds and continuing her journey of musical exploration. Listeners can anticipate a collection of tracks that build upon the innovative foundation laid by her previous work, offering new perspectives and further showcasing her versatility as a pop singer. With her relentless drive, a clear artistic vision, and the unwavering support of those closest to her, Jessie Berg is undoubtedly poised for an even brighter future in the music industry. Her story is one of courage, self-discovery, and the powerful synergy of friendship and ambition, inspiring both aspiring artists and music lovers alike to embrace their authentic selves and pursue their dreams without compromise.