Wiz Kahalifa performs at Reggae Sumfest 2014

Wiz Kahalifa performs at Reggae Sumfest 2014 in Montego Bay, Jamaica on July 19, 2014.

A.Gilbert Bellamy

"I'm always nervous performing at home because Jamaicans are tough people to please but I am very happy with tonight's outcome," revealed Jamaica’s Tessanne Chin – and NBC’s The Voice season five winner – minutes after delivering a flawless, headlining set at Reggae Sumfest in Montego Bay. Surrounded by her family and management team, the exceedingly gracious Chin posed for numerous photos with fans prior to reminiscing with Billboard about her Sumfest debut in 2007, which coincided with the release of her breakthrough single "Hideaway." "It felt like my career was just beginning back then so to return this year and perform "Hideaway" alongside songs from my new album 'Count On My Love' is a dream come true."

Reggae Sumfest was developed to increase visitor arrivals to Jamaica during the traditionally low summer tourism season; over three nights Sumfest annually attracts nearly 25,000 patrons from around the world, according to Executive Director Johnny Gourzong. Held at the open-air Catherine Hall Entertainment Complex Sumfest’s 22nd annual staging, July 17-19, presented forty Jamaican dancehall and roots reggae artists alongside international acts, Jason Derulo, Wiz Khalifa and Future.

Prior to Derulo’s well-received set on Friday’s International Night 1, which included a guest appearance by 2007 American Idol winner, his fiancé Jordin Sparks performing their hit "Vertigo," he shared with Billboard his fondness for beef patties – the humble Jamaican fast food staple – and a lifelong love of reggae. "My father lived here for 12 years and Bob Marley’s music was played in our house, so there’s always a hint of reggae in my music. I’m really excited to perform for my Jamaican fans," Derulo said.

Wiz Khalifa told Billboard he was humbled by Jamaica’s love for him and expressed interest in working with local artists. "Reggae’s message brings people together and that’s been really influential to me; if I could collaborate with any artist here it would be Beenie Man,” he acknowledged.

Also on Friday night, upcoming Rastafarian sing-jay Jesse Royal made his impressive Sumfest debut and roots reggae sensation Chronixx delivered a beautifully nuanced, mesmerizing set while Jamaica’s Sean Paul triumphantly returned to Sumfest after a 10-year absence with an energetic performance on Saturday’s International Night 2.

Yet, it’s Sumfest’s Thursday Dancehall Night that dependably pulled the largest crowd, estimated by Gourzong this year at 12,000. Highlights included a riveting lyrical display by Agent Sasco, Bounty Killer’s incisive social critiques and female singer Spice, who donned male drag to attain deserved props in the testosterone-laden genre.

As the tropical sun rose over Catherine Hall minutes before 6 AM, I-Octane held the majority of the crowd in place with renditions of the numerous hits that earned him the night’s prestigious closing slot. Shortly after leaving the Sumfest stage, I-Octane wentto the studio with producer DJ Frass and recorded "Jah Mi Seh" aimed at his detractors, especially Mr. Vegas who continually criticized the selection of I-Octane for Dancehall Night’s crowning position. "I am the only artist in Sumfest's history besides Beenie Man to close Dancehall Night for two consecutive years, which is a great accomplishment for a young artist," I-Octane told Billboard. "Even if I am working overseas, I come back to Jamaica for Sumfest, it brings visitors to Jamaica and is an important showcase for our artists locally and globally."