Roy Woods Shows Off a New Side of Himself with 'Dark Nights' Short Film

Roy Woods is thriving.

“The energy’s high right now. I feel back in motion after a couple of years – it feels like I pressed the restart button,” he tells Billboard Canada.

The Toronto R&B singer and rapper released his new EP, Dark Nights, in April, and it showed off a new side of the OVO Sound-signed artist.

At nine tracks, Dark Nights is a bold and unfiltered reflection on betrayal, heartbreak and emotional survival. It debuts a more vulnerable side of the Toronto singer-songwriter, who opens up about some of the darkest moments he’s faced – and how he has learned to live through them.

With such complex emotions on the line, Woods took his aptly-titled EP and created a short film based on the project’s major themes. The 20-minute short film premiered on Thursday, June 12, at NXNE, followed by a Q&A with Billboard Canada’s National Editor Richard Trapunski.

“My manager, Banks, and I wanted to show this type of pain in a different way than the traditional music videos,” Woods shares. “We wanted to showcase the art in a different light.”

Before the EP’s release, he recalled having initial conversations about the short film at the top of the year. Woods and his collaborators noted that the tracklist flows into one another, boldly telling a story from start to finish.

“There's so much depth in the songs,” he explains.

While Woods had dabbled in acting as a child, making a short film was completely new territory. The project took four days to film and consisted of all-day shoots – not to mention managing a robust cast and crew. Yet, he fondly recalls the experience. “The energy was on 10. There was a lot of excitement, and everybody was ready to do the best job possible.”

With dreamy nighttime hues and dimly lit rooms, Dark Nights follows Woods through a relationship that transforms into a complicated dynamic that includes betrayal, unplanned pregnancy and big existential questions. Based on a true story, Woods channels somber energy and anguish in his first major acting role.

He cites the darker, moody era of late 2010s Toronto R&B music as inspiration. “We didn’t bring it back, but kind of reignited the flame. We stay true to its essence and bring it in a modern light,” he says. “We wanted to stay true to that Roy Woods aesthetic.”

He describes the aforementioned artistic vision as “late night driving R&B moody music, that’s balanced with songs that are good for parties and good vibes.” It’s an energy Woods has mastered in his almost-decade-long career.

In 2015, Woods signed with Drake's OVO Sound record label and skyrocketed onto the scene mere months later when his track “Drama,” from his debut EP, Exis, was released in collaboration with the beloved Toronto rapper. The EP peaked at No. 27 on Billboard’s Top R&B/Hip-Hop Albums, marking his first placement on the chart. Woods continued on an upward trajectory, as his following full-length efforts, Waking at Dawn and Say Less,also earned him spots on the Billboard 200 and Canadian Albums charts.

“I'm so grateful for my music to reach those heights. When it happened, it made me realize that I was an artist of this calibre,” Woods explains. But it doesn’t change how he approaches his current work. “Because if I did, then I'm chasing something that doesn't feel true to me. Those songs were created by me expressing, writing and feeling good about making music, with no pressure to make it.”

Woods cites Drake and PartyNextDoor as two of his biggest influences, so he feels lucky to be their label-mate. Of his relationship with OVO, Woods praises the record label for their mentorship and guidance, which has kept him away from the shifting, often pressured expectations of emerging in the music industry.

“I didn't want to change who I was in the music that I make. At OVO, we’re keen on making music that is true to ourselves and the people around us,” he shares.

Now, 10 years on, the concept of embarking on a creative project with no expectations became a mainstay for Dark Nights — the EP and the short film. “This music that I've been making lately, and now the short film feels so good because I've been in the moment. I'm creating to create, [and] I'm loving it. I'm having fun with it again.”

He credits this flexibility to his “very personal” relationship with fans. “I'm so grateful to [them] because they stand by me, learning, growing and loving myself now compared to the person and the artist that I was earlier in my career,” Woods says.

Although he’s Brampton-born, Woods’ love extends to Toronto, the city he came up in. “I receive a lot of respect when I’m in my city. The love is always different than any other place,” he explains. “I’m learning that I’m an important figure to not only the area I grew up in, but the entire city of Toronto.”

Now that Woods has pressed the restart button, he assures listeners that he isn’t going anywhere. With aspirations to stay in his acting bag, he’s going to continue exploring creative projects outside of music. “We're flooding the gates. You're gonna get annoyed with Roy Woods, and that's what I want right now. I'm going all the way, you know? Godspeed.”