Jay Whiss

Jordan Whiston (September 24, 1992 – March 22, 2025), better known by his stage name Jay Whiss, was a Canadian rapper and songwriter from Toronto, Ontario. He first gained international attention after the release of the single "Watch This", which appeared on OVO Sound Radio in late 2015. Whiss also appeared on the Noisey documentary 6IX RISING (2017), which showcased hip hop culture in Canada. He is one-third of the hip hop collective Prime Boys, alongside Jimmy Prime and Donnie. Prime Boys released their debut studio album Koba World on July 27, 2018; the album received a 9/10 score by Exclaim!. Whiss was also featured in the short film Remember Me, Toronto (2019) by Mustafa the Poet.

He embarked on his solo venture in 2019 with the release of his EP Dark Clouds, after being signed to Universal Music Canada. The 3-track EP, which served as a prequel to his upcoming album, contained the single "Every Night", featuring vocals from Jimmy Prime and Safe, and "Dark Cloud", which was also confirmed to be the first single from the upcoming album. Jay's debut studio album Peace of Mind was released on March 3, 2020. The album was supported by the singles "Valet", featuring Puffy L'z, "Lay Low", featuring Donnie, and "Mind in a Maze". It received an 8/10 rating by Exclaim!.

Whiss died in March 2025 from brain cancer.

We were just chilling one day at 176 and he asked me to go to the studio. I booked us a session at Wellesley Sounds and there were probably 20 of us who walked over there. We had the session and everything with Donnie just started from there.

Jay Whiss was born in 1992 to an Irish mother and Vincentian father. An only child, he was raised by his single mother who moved to St. Lawrence, Toronto when he was a week old. He has stated that he lived in a number of different places whilst growing up. Whiss claimed he had a typical childhood, playing hockey and soccer, and in 2006, at the age of 11, he moved to the opposite side of the city but still hung around in the Esplanade area of Toronto. He attended numerous high schools but eventually dropped out after being 4.5 credits short of graduating. Whiss mentioned that he had no musical influence in his family, but his mother, who was a part-time employee at HMV, used to bring numerous musical CDs from different genres home, which drew him to like music. He recalled his father saying to him: "you know the lyrics to every song but don't do your homework" in regards to his childhood. His earliest musical influences include Ludacris, Missy Elliot, The Notorious B.I.G., and Jay Z. He has also noted Canadian artists Solitair, Kardinal Offishall, and Point Blank amongst his influences.

Whiss decided to start rapping in the summer of 2010 at the age of 17, as a way to express himself. He released his first single "Chasing a Dream" on January 3, 2011, at the age of 18 via WorldStarHipHop, followed by the single "2011 Til Infinity" on February 6 of the same year. Both singles were shot with long-time Prime Boys affiliate and music video director Tristan Prime but received little recognition. Alongside Prime Boys, Whiss and his entourage first attracted local attention in St. Lawrence in 2013 and gained national attraction with the single "I Heard", produced by Eric Dingus and released on November 17, 2014. Prime Boys' most prominent member at this time, Jimmy Prime, gained the group considerable attention for coining the nickname "The Six" for Toronto, a term that has been broadly accepted by rappers such as Drake. Jimmy Prime released his mixtape Block Boy in July 2015, featuring Whiss on the track "Best One". The release also prompted a photoshoot by Vice in the following month, which gained the group some notice on a national scale. Jay Whiss came to the attention of record label manager Oliver El-Khatib, who added Whiss' single "Imagine Us" to Episode 5 of OVO Sound Radio in September 2015. In November 2015, Whiss released the single "Watch This", produced by Lani Christ, and followed it up with a music video directed by Tristan Prime. The video featured cameos from his crew members Jimmy Prime, Donnie, and Esplanade associate Safe. He then went on to release the track "Need it all", which featured Jimmy Prime and was produced by Eric Dingus. Dingus was later signed by Drake, and added the song to Episode 42 Of OVO Sound Radio.

In early 2016, Halal Gang member and Esplanade native Safe drew the attention of Drake. Since gaining the approval stamp from Drake himself already in the previous year, Whiss remained relatively quiet in terms of making music. However, a few months later, Whiss released the single "Driven", which featured Safe and was produced by 1mind. The song "Full Circle", with Donnie, Puffy L'z, Smoke Dawg, Safe, and Jimmy Prime, showcased a new supergroup forming in Toronto with all 3 Prime Boys and 3 of the Halal Gang members. The song was released in September 2016 and quickly went viral, amassing over a million views in a year. The group were labelled the "all-star team" of Toronto street rap. The song was another of Whiss's that made it on OVO Sound Radio, this time on Episode 34. Whiss and the Prime Boys also became good friends with Toronto producer Murda Beatz in 2016, and the latter provided production for the artists' work. Murda Beatz released his mixtape Keep God First on December 10, 2016, featuring Jay Whiss on the track "Brown Money".

Jay Whiss officially made his debut feature on Spotify's Northern Bars playlist with the single "Welcome to the Life", which was released in May 2017 and produced by Murda Beatz. The Northern Bars Playlist is part of the RapCaviar series, which focuses on Canadian Hip Hop. Toronto's uTOpia music festival was held in June 2017 and showcase a new generation of artists in the General Toronto Area. Jimmy Prime, who was one of the main performers at the festival, brought out Jay Whiss and Donnie, who performed alongside Smoke Dawg, Puffy L'z, and Mo-G. The event was rated 7 by Exclaim!, who described Prime Boys and Halal Gang's performances as playing off of each other's energy. Whiss also appeared in the Noisey documentary 6IX RISING, which looks into the rising hip-hop scene of Toronto after the blockbuster success of Drake and The Weeknd. The film premiered to a limited audience at Hot Docs Ted Rogers Cinema on November 16, 2017.