Machel Montano’s Quest for Road March Glory: “Encore” Aims to Break Historic Record

The Trinidad and Tobago Carnival landscape is buzzing with anticipation as soca legend Machel Montano prepares to release his Road March contender “Encore,” setting the stage for what could be a historic moment in Caribbean music. Currently tied with the late calypso icon Lord Kitchener at 11 Road March titles each, Montano stands on the threshold of breaking a record that has endured for nearly five decades.

The Battle for Road March Supremacy

The Road March competition represents one of Trinidad Carnival’s most coveted honors, awarded to the song played most frequently at judging points during the Monday and Tuesday parade route. Since officially beginning in 1932, this prestigious title has become the ultimate measure of a song’s impact on Carnival culture, determining which track truly captures the spirit of the nation’s greatest celebration.

Montano’s journey to this pivotal moment began with his first Road March victory in 1997 with “Big Truck,” launching a career that would span multiple generations of Carnival masqueraders. His subsequent wins include memorable anthems such as “Jumbie” in 2007, “Like Ah Boss” in 2015, and the collaborative triumph “Famalay” with Skinny Fabulous and Bunji Garlin in 2019. Most recently, his 2025 victory with “Pardy” brought him level with Kitchener’s seemingly untouchable record.

Just behind these two giants in the Road March hierarchy sits Superblue (Austin Lyons) with ten titles, followed by the Mighty Sparrow (Slinger Francisco) with eight wins. This elite group represents the aristocracy of Carnival music, but only Montano and Kitchener have reached the rarefied air of double-digit victories.

“Encore”: A Song Born from Success

The release of “Encore” reunites Montano with the creative powerhouse behind “Pardy”—songwriter Andre Jeffers and production duo XplicitMevon (Mevon Sooden) and Kyle Phillips of Badjohn Republic. This collaboration proved instrumental in delivering Montano’s 11th title, creating what many described as a defining Carnival moment that resonated far beyond the traditional fete circuit.

According to Montano, developing “Encore” presented unique challenges. The creative team faced what seemed like an impossible task: following up the massive success of “Pardy” while maintaining the standard of excellence that Carnival audiences demand. Montano described the process as emerging through what he called “divine intervention,” as the team wrestled with how to advance from their previous achievement.

The song features what Montano calls quotable lyrics set atop a mas-ready drum cadence designed to energize masqueraders along the parade route. Drawing inspiration from his journey to the pinnacle of soca music, “Encore” reflects themes of perseverance and excellence that define both Montano’s career and the competitive spirit of Road March itself.

Honoring Kitchener’s Unmatched Legacy

Despite standing on the verge of surpassing Kitchener’s record, Montano remains deeply respectful of the calypso legend’s contributions to Caribbean music. Born Aldwyn Roberts in Arima, Trinidad and Tobago in 1922, Lord Kitchener earned the title “The Grand Master of Calypso” through his profound impact on the art form.

Kitchener’s Road March dominance spanned from 1946 with “Jump In The Line” to his final victory in 1976 with “Flag Woman.” His reign included classics that have become part of Trinidad’s cultural DNA, including “The Road” in 1963, “My Pussin” in 1965, and “Miss Tourist” in 1968. Between 1963 and 1976, Kitchener captured an astonishing ten Road March titles, establishing a benchmark that seemed destined to stand forever.

Beyond Road March victories, Kitchener’s influence extended to steelpan music, where his compositions became favorites for Panorama competitions. His melodies were specifically crafted for steel orchestras, earning him 18 Panorama victories as a composer—more than any other songwriter in the competition’s history. Artists including Calypso Rose, David Rudder, and Black Stalin all benefited from his mentorship, cementing his role as not just a performer but a cultural architect.

Montano emphasizes that his pursuit represents building upon foundations laid by Kitchener rather than eclipsing them. He acknowledges that Kitchener’s era presented different challenges, including less advanced production technology, the need to travel internationally to promote calypso, and the burden of single-handedly writing and constructing his Road March winners. Montano’s collaborative approach, working with multiple producers, songwriters, and creative teams, represents an evolution in how soca music is created for the modern Carnival landscape.

The Evolution of Road March Music

The contrast between Kitchener’s calypso-dominated era and Montano’s soca revolution illustrates the genre’s transformation over five decades. Kitchener worked primarily with steelbands and traditional calypso arrangements, crafting songs that relied on clever wordplay, social commentary, and melodies designed for acoustic instruments.

Montano’s Road March victories chart soca’s evolution from horn-driven anthems to digitally produced road energy that incorporates influences from dancehall, pop, and EDM. His wins span the genre’s modern development, from the late 1990s breakthrough of “Big Truck” through the collaborative, internationally-flavored productions of recent years.

The 1977 victory by Calypso Rose with “Give More Tempo” marked a turning point, introducing synthesizer technology and brass bands to the Road March formula. This shift, combined with Shadow’s groundbreaking 1974 win with “Bass Man,” fundamentally refocused the competition toward the dance-oriented soca sound that would come to dominate Carnival’s musical landscape.

What Drives the Soca Monk

Standing at this historic crossroads, Montano insists his motivation extends beyond accumulating titles. He describes himself as chasing creativity and excellence rather than records, viewing each new production as an opportunity to push soca music forward. His ultimate goal involves changing messages and singing beyond traditional Carnival vibrations, aiming to position soca as a globally recognized genre capable of diverse artistic expression.

Montano’s vision for the future includes his retreat space where he develops new musical concepts, grows food, and creates ideas for advancing Caribbean music. Far from retirement, he views this as a cycle of renewal—retreating to plant creative seeds, allowing them to develop, then returning to share the harvest with audiences worldwide.

The Road Ahead for Trinidad Carnival 2026

As Carnival 2026 approaches, all eyes will be on whether “Encore” can propel Montano to his record-breaking 12th Road March title. The competition remains fierce, with new generations of soca artists vying for their own place in history. Bunji Garlin finished second in 2025 with “Carry It,” demonstrating that veteran artists continue challenging for the crown alongside emerging talent.

The Road March title carries more than prestige—the 2025 winner received a cash prize of $250,000 plus additional prizes from sponsors. More importantly, the title cements an artist’s legacy within Trinidad and Tobago’s cultural fabric, ensuring their contribution to Carnival will be remembered for generations.

Whether Montano succeeds in breaking Kitchener’s 50-year record or another artist captures the 2026 crown, the Road March competition continues serving as the ultimate test of what resonates with Trinidad’s Carnival masses. As thousands of masqueraders take to the streets in February 2026, the music playing at judging points across Port of Spain, San Fernando, and beyond will determine who joins the pantheon of Road March champions.

For Machel Montano, “Encore” represents both a culmination of decades of dedication to soca music and a statement that even after 11 victories, the pursuit of excellence continues. As he noted when discussing the creative process, true artistry involves constantly reaching for something better than the last performance—a philosophy that has guided him from that first “Big Truck” victory in 1997 to this moment of potential history-making in 2026.

The stage is set, the song is ready, and Trinidad waits to see if the soca monk can add one more title to his legendary career.

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