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Shaggy & Massari: Why

Reggae hitmaker Shaggy has taken time off work with Sting to join Canadian singer Massari on a breezy and catchy single. Given that Caribbean-tinged pop tracks are hot these days, this one might blow up.

Shaggy & Massari: Why

By Kerry Doole

Shaggy & Massari - "Why" (300 Entertainment/Brooklyn Knights Entertainment): Reggae/pop hitmaker Shaggy "(Oh Carolina", "Boombastic") has been in the news a lot of late, given his collaboration with Sting on their duo album, Don't Make Me Wait., and a recent Grammy Awards appearance. He has also found time to record a joint track with Canadian singer Massari, and it is a tasty confection.


Shaggy confirms that he is a master of dancehall flow, and his stylings contrast nicely with Massari's smooth vocal on the breezy and uptempo cut. Lyrically, there is some standard innuendo, as on "I want a bit of what you've got," but the tune is relatively G-rated.  This kind of Caribbean-flavoured crossover track is definitely in vogue these days, so its commercial prospects are rosy.

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Massari has enjoyed international success with other recent singles, with videos for 2017 tracks “So Long” and “Done Da Da” attracting over 60 million views on YouTube. He also teamed with hit Canadian rapper Tory Lanez on the track "Number One" a few months back.  He has yet to break through Stateside, but this may help boost his chances.

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EMPIRE's Tina Davis (left) and Girl Connected's Lola Plaku at Conversations with the Pros at Toronto Metropolitan University in Toronto on March 28, 2025.
Courtesy of Girl Connected

EMPIRE's Tina Davis (left) and Girl Connected's Lola Plaku at Conversations with the Pros at Toronto Metropolitan University in Toronto on March 28, 2025.

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EMPIRE President Tina Davis Gives Strategic Advice to Women in Music at Girl Connected's New Speaker Series

On Friday (March 28), the president of EMPIRE, the Bay Area-independent label and music company, came to Toronto for Conversation with the Pros offering tangible advice to the mentorship program's community. Davis also spoke to Billboard Canada about her impressive journey in the industry.

Girl Connected has launched a new series that connects the next generation of women in Canadian music with powerhouse executives for the global industry.

On Friday (March 28), Tina Davis, president of EMPIRE, sat down with Girl Connected founder and music industry veteran Lola Plaku at Toronto Metropolitan University for the first in-person Canadian edition of Conversations with the Pros (Billboard Canada was a supporting partner). The series brings in inspiring music industry figures from Girl Connected's international network to talk about their journeys and offer actionable information and advice to help the budding music professionals develop their skills and reach the next level of their careers.

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