A Drake and team YouTube screenshot.
A Drake and team YouTube screenshot.

Prism Prize Eligible Video Drake: When to Say When / Chicago Freestyle ft. Giveon

The 2020 Prism Prize for Best Canadian Music Video was awarded to Peter Huang, for his clip for Jessie Reyez's Far Away. We will continue to profile noteworthy Canadian videos that were eligible for the Prize, including this one from an international music superstar that features a young American R&B singer. 

Drake – When to Say When / Chicago Freestyle ft. Giveon

Toronto’s Very Own, Drake, is a famed Canadian rapper, singer, songwriter and entrepreneur. Dominating the flow and influence of popular culture, Drake is known as an inspiration to many fans and music artists alike. Aiming to achieve similar strides in his level of success and influence. Drake is also credited for popularizing the Toronto sound specifically, birthing a revolutionary culture for future generations to continue to rise out the city. 

When to Say When / Chicago Freestyle are two featured classics on Drake's mixtape Dark Lane Demo Tapes that pay tribute to notable rappers. When to Say When features a sample of Song Cry by Brooklyn’s Finest, Jay-Z , while Chicago Freestyle opens from Eminem’s flow with Superman. The mixtape consists of prior released SoundCloud tracks and new releases, which are now available on current streaming platforms like Apple Music, Spotify, etc. Chicago Freestyle peaked at No. 14 on the Billboard Hot 100.

Theo Skudra, starting as a digital-image technician for Drake’s music video for Marvin’s Room, landed his senior gig as one of the lead creative Directors / Cinematographers for his outstanding visual delivery. His shooting style composes of vivid photojournalism, which encapsulates authentic moments or aesthetically pleasing lifestyle images. His main experience is field work, which consists of capturing lifestyle on long tour nights, moments in the studio, and everything in between. Skudra always has his camera around Drake, aiming to capture the best candid moments, or promotional content that can be used at a later time. 

Staying true to Skudra’s vision, When to Say When opens off with Drizzy in his Toronto mansion indulging in a smoke and overlooking the city from his balcony. It further begins to showcase him dancing, riding through Toronto, stopping at the jeweller’s and cashing out with his team. Skudra doesn’t only capture Drake at home in riches, but he is featured by the Brooklyn Bridge in other establishing scenes, as well as the impoverished Brooklyn Housing Community, Marcy Houses –– known as the projects which birthed music mogul, Jay-Z. 

When transitioning to Chicago’s Freestyle in the joint video, the scene is established with a contradictory shot of Toronto’s downtown core. Nonetheless,  Skudra creatively sets the scene by using slow visuals in-sync to slowly stricken piano chords and vocals of featured artist, Giveon, to view Drake’s nightlife in Toronto. Panning from a view of the city, to Drake leaving his gated driveway, to him on the Gardiner, in the studio, or in his safe; the video serves to showcase everything Drake is familiar with on a daily basis. Skudra’s visuals definitely tell a story, which is edited in a way that caters to the reality of Champagne Papi. 

Artists: Drake / Giveon

Director: Theo Skudra

Producer: Christian Tyler

Cinematographer: Theo Skudra

Editor: Theo Skudra

Production Company: Colossale

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