The universe often presents remarkable alignments, and the current cultural landscape is no exception. The unveiling of a new documentary chronicling the illustrious career of Machel Montano, widely dubbed the "Michael Jackson of the Caribbean," coincides with a significant resurgence of the original Michael Jackson’s music on the Billboard charts. This timely convergence highlights the enduring impact of musical pioneers and their lasting influence across generations and genres.
On Friday, May 29, Like Ah Boss: Journey of a Soca King – Machel Montano made its official debut in the United States across all digital platforms. Co-directed by Bart Phillips, founder of Sunseeker Media, and Montano’s manager, Che Khotari, the film eschews a purely retrospective glance, instead focusing on a pivotal year in Montano’s career: 2015. During this intense period, Montano documented his relentless journey, delivering an astonishing 16 high-energy performance sets within a single seven-day span amidst the vibrant Carnival season. This extraordinary feat served as a prelude to subsequent milestones, including a prominent appearance on the Coachella main stage in 2016, impactful collaborations with global music sensations like Ariana Grande ("All My Love") and Ashanti ("The Road"), and a memorable performance at Sadhguru’s Maha Shivratri Festival in India in 2022.
At the heart of the documentary is a Machel Monday performance, witnessed by an electrifying crowd of over 25,000 fans. The film’s narrative is predominantly underscored by Montano’s 2015 anthem, "Like Ah Boss." This track has garnered substantial traction, amassing nearly 20 million official on-demand U.S. streams to date, according to Luminate. While the documentary undeniably celebrates Montano’s triumphant journey, it also offers a remarkably candid and introspective portrayal of his life and career.
Like Ah Boss: Journey of a Soca King does not attempt to encapsulate Montano’s four-decade career within its 78-minute runtime. However, the film skillfully navigates the more challenging chapters of his storied life. It delves into the profound impact of the devastating collapse of a VIP stand during his 2000 Real Unity concert, an incident that resulted in injuries and significant legal repercussions. The documentary also candidly addresses Montano’s personal battles with depression and other brushes with legal challenges. By presenting an expansive view of his past 40 years, the film imbues the inherently effervescent spirit of soca music with a palpable weight and gravity.
This comprehensive lens is particularly fitting for a journey that commenced when the King of Soca was merely a child. At the tender age of nine, Montano graced the stage at New York City’s Madison Square Garden, opening for legendary calypso artists such as Mighty Sparrow. Years of local acclaim, chart-topping singles, and anthemic carnival road songs followed. By 2012, Montano had achieved a remarkable "Triple Crown" victory, with "Mr. Fete" securing the Groovy Soca Monarch title, and "Pump Your Flag" claiming both the Power Soca Monarch and Road March victories. His international recognition solidified in 2014 when he clinched the Soul Train Music Award for Best International Performance with "Ministry of Road (M.O.R.)," notably triumphing over contemporary crossover hits like Sam Smith’s "Stay with Me." This period of acclaim culminated in the iconic year of 2015, which the documentary prominently features.
Today, Machel Montano stands as Trinidad and Tobago’s undisputed all-time Road March champion. His hit single "Encore" marked his twelfth career victory in this prestigious category, officially surpassing the long-standing record of 11 held by the late Lord Kitchener. Having already etched his name multiple times into the annals of Caribbean music history, Montano’s current ambition is to propel soca music onto the global stage. The initial phase of this endeavor involves the successful completion of his ongoing Encore Tour, which commenced in Jamaica in April and includes highly anticipated performances at New York’s Central Park on August 8th and 9th.
In an exclusive interview with Billboard, Machel Montano offers an intimate glimpse into the making of his new documentary, discusses his early strategies for engaging a younger demographic by drawing inspiration from groups like New Edition, and reveals the global superstar who remains at the apex of his collaboration wish list.
The Genesis of a Cinematic Journey
When did you decide you wanted to shoot a documentary?
The inception of the documentary project dates back to 2015. We recognized the profound significance of that year, a period marked by personal transformation. My manager, Che Khotari, joined my team in 2014, and I shared my vision with him: "I want you to manage me to zero. Take me back down to my basic self, and then let’s rebuild it all over again. But first, you need to come on the road and experience Carnival."
In 2015, our focus was on reclaiming the Road March title, and the song "Like Ah Boss" exploded. It was an incredibly demanding year, also coinciding with the release of the Monk Monté album. I embraced a new persona, and my guiding principle became "Cooperation over competition." I was eager to forge collaborations with emerging artists and international figures to expand the reach of soca music globally. Consequently, we decided to bring cameras along to document our pursuit of Road March glory, our subsequent tours, and the unfolding events of the following year. We encountered various challenges and triumphs, and the cameras continued to roll until 2020.
Timing the Release: A Strategic Approach
Why did now feel like the right time to start sharing this with the world?
A significant milestone in my career is approaching in 2026, where I will hold the record for the most Road March titles, surpassing Lord Kitchener’s 50-year-old achievement. While this wasn’t an initial objective, it gradually became a tangible reality, and we dedicated immense effort to attain it. Presently, our primary focus is on achieving international recognition for soca music. We aim to cultivate a new sonic identity as the Caribbean music scene experiences a period of unprecedented synergy, encompassing genres like jab, Dennery segment, and bashment. There’s a palpable sense of unity emerging within the region.
Reflecting on a Legacy: The Power of Retrospection
What was it like for you to watch these years of your life back 10 years later?
I rarely dwell on the past or bask in past glories and victories. Our work ethic has been relentless, so looking back provides a clearer perspective on the timeline and the universe’s intentions for me or through me. It allows for a deeper understanding of the music’s impact on people and its most significant contributions. It was profoundly inspiring to revisit pivotal moments, such as meeting Sadhguru and performing at Coachella with Major Lazer, featuring an Ariana Grande collaboration. This retrospective offered renewed motivation to push forward. Despite having dedicated 40 years to my craft and potentially being in a phase of winding down, it feels like a new beginning.
Unveiling the Unseen: Deeper Thematic Exploration
What do you wish you could have explored more in the documentary?
I wish I could have elaborated more on the strategies I employed to make soca music resonate with younger audiences. In my early career, the typical audience comprised individuals in their 50s and 60s, often dressed in suits and carrying canes. I often wondered, "Where were my peers?" I would attend clubs where the music of choice was dancehall, hip-hop, and R&B acts like New Edition.
As a fervent admirer of Teddy Riley and Heavy D, I would use my Mac computer to recreate elements like the snare sounds from "Poison" and incorporate them into my performances to capture the attention of younger listeners. It was akin to a mother subtly administering medicine by disguising it as an airplane; I would subtly introduce hip-hop influences into a soca set. Furthermore, I collaborated with prominent Jamaican artists such as Shaggy, Beenie Man, Red Rat, and Mr. Vegas to infuse soca and our local culture with a contemporary edge. Naturally, I also recognized the need to inject an element of sensuality into the performances – shedding shirts, dynamic waist movements, engaging with the audience, and incorporating visually appealing elements.
The Dual Nature of Fame: Battling Depression Amidst the Spotlight
You touched on this in the documentary a bit but talk to me about creating soca music while battling bouts of depression.
This is the inherent challenge of operating at extremes; prolonged periods of intense activity inevitably lead to a significant slowdown. A substantial portion of soca music is centered around relentless energy, revelry involving alcohol and romantic encounters, and at times, the use of cannabis to enhance these experiences. When these elements are pursued at such a high level from a young age, the body inevitably experiences wear and tear. A depleted physical state impacts nutrient levels, leading to a decline in physical well-being, and subsequently, mental and emotional health begin to suffer. While I am fortunate to have a supportive family, it was virtually inevitable that at some point, my capacity to sustain this demanding lifestyle would diminish.
The paramount pressure within the soca music industry is the expectation of annual output. There is no allowance for two or three-year gaps between album releases. Failing to produce a hit in a given year can lead to obscurity. This constant pressure and fear are pervasive. When one experiences a downturn, it’s not merely about the absence of hits; it also entails producing albums that gather dust, unsold. This results in financial losses. Consequently, artists often depart Trinidad Carnival, heading to Jamaica, Toronto, New York, and London, then participating in Miami Carnival in October, leaving only November and December to create an album. My ambition extended beyond a single hit; I aimed to produce albums that explored diverse themes catering to different communities. Additionally, I committed to my "Machel Monday" concerts, which placed an additional layer of pressure on myself, ultimately leading to burnout. At times, it is essential to grant oneself the necessary time and space for recovery.
The Relentless Pace of Performance: A Question of Repetition
16 shows in seven days. Would you ever do it again?
We actually experienced a similar period this year in our pursuit of breaking the Road March record with "Pardy." However, if I were faced with the prospect of performing 16 shows in seven days to elevate soca music globally or to win a Grammy, I would undertake it. Nevertheless, I do not believe such an approach is presently necessary. I feel it is crucial to present the narrative of soca music, much like Bad Bunny has done for the culture of Puerto Rico. I envision a level of Caribbean unity that must be achieved, encompassing Haiti, Cuba, and all the islands we hold dear, given the profound similarities in our musical traditions.
The Encore Tour and Beyond: A Vision for the Future
What can people expect from the Encore Tour?
Audiences can anticipate a truly enjoyable experience. I am immensely grateful to have both a young and an older demographic as my audience. I eagerly anticipate concluding this tour and embarking on the next 20 years of Machel Montano’s career, though patience is key. Attendees will have the opportunity to experience the full spectrum of my hits, and I have curated a unique song for each new show that I have never performed before. The tour promises a comprehensive journey through four decades of Machel Montano’s musical evolution.
For the fifth decade of your career, what do you want to prioritize?
My priorities for the next decade are global relevance and fostering healing through music. My primary objective is to inspire the world to dance. I aim to identify the common threads that connect soca, bouyon, Dennery segment, zess, dembow, reggaeton, and even Afrobeats and emerging trends in India. I firmly believe that soca music embodies the essence of unity.
The Royal Succession: Identifying the Next Generation of Soca Royalty
We know you’re the King of Soca. Who’s the prince? Who’s the princess?
There are numerous talented artists poised to ascend, and each of them will undoubtedly become the Queen and King of Soca in their own right. Artists such as Kes, Voice, Yung Bredda, Patrice Roberts, and Nailah Blackman, along with Nessa Preppy, represent a significant wave of talent from various islands. Faith Callender, Trilla-G, 1t1, Little Boy, and Jordan English are also making their mark. The entire Grenada contingent, including artists like Muddy, Lil Kerry, and V’ghn, are contributing to this vibrant scene. There is a multitude of emerging faces and individuals fearlessly experimenting with the genre.
A Wish List for Global Collaborations
Who’s left on your list of dream collaborators?
Rihanna, give me a call! I am actively writing songs for Rihanna and seize every opportunity to reach out to her. I would be thrilled to collaborate with her on a soca track. She has achieved success in every genre she has tackled, and power soca is the remaining frontier. I have a song in my repertoire that I am eager to present to her once I conclude my tour. I deeply admire her dedication and focus.
I am also a great admirer of Tems and am keen to work with Moliy. We were close to releasing a remix of "Backie." Wizkid is a good friend, and I am hopeful we will collaborate in the future. Additionally, I am interested in undertaking Afrobeats and Indian collaborations, as I believe these musical elements share a strong affinity with soca music.
Future Endeavors and Artistic Evolution
What else can we expect from you in 2026?
My current focus is on these performances and the release of this documentary, as I believe it offers a valuable opportunity to impart knowledge to younger artists. Following this period, I intend to step back at the end of the year and enter a period of artistic introspection. I have undertaken this hiatus two or three times in my career, and each instance has resulted in significant personal and creative transformation. I am also actively engaged in developing new musical projects.
The Echo of a Legend: Reflecting on Michael Jackson
Speaking to the Michael Jackson of the Caribbean, have you seen the Michael Jackson biopic yet?
Absolutely! I found it to be exceptionally well-executed. Jaafar Jackson’s performance was undoubtedly Oscar-worthy, demonstrating remarkable precision. I understand the narrative choices made in the film’s storytelling. I believe this film has the potential to be the "Fast and Furious of music movies," suggesting the possibility of numerous sequels. The quality of the acting, particularly from Colman Domingo and Nia Long, was outstanding. For future installments, I hope the narratives will continue to evolve organically, as Michael Jackson was an artist I deeply admired. His artistic DNA is interwoven into every facet of my work.
Imagining a Biopic: The Quest for the Perfect Portrayal
When they make your biopic, who do you want to play Machel Montano?
It would likely require a ensemble cast of actors to authentically portray the various stages of my life. When the time is right to tell this story, we will need to identify individuals capable of delivering truly compelling performances. I am confident that such talent exists, and I eagerly anticipate that narrative being presented. However, there are still several significant achievements to accomplish, including topping the Billboard charts and securing Grammy Awards. I envision repackaging the history of Carnival into a lavish $100 million Las Vegas production, a fitting way to conclude my career, akin to Frank Sinatra.
