This week, Billboard is celebrating the music video with a week's worth of content that looks at the past, present and future of the video, at a time when it seems to be as relevant as ever. Here, we spoke to Director X about some of the most iconic videos he's helmed during his two-decade career.

In the 20 years since his late-'90s debut, Director X has established himself as one of this generation's most legendary music video directors. From his signature horizontal opening scenes to his consistent celebrating of his Caribbean roots, the Toronto native's visual innovation has brought hits of many artists across genres to life -- Fifth Harmony's "Work from Home," Kendrick Lamar's "King Kunta," Ciara's "Body Party," Justin Bieber's "Boyfriend," Nelly Furtado's "Promiscuous," Usher's "Yeah" and dozens of others. Yet there is a less-memorialized video the former Hype Williams protégé points to as helping catapult his career.

"The big one was Redman’s 'I'll Bee Dat!' [in 1998]. The concept was fun and it really connected," X explains to Billboard. "And it was one of those things in the age of music videos where it was -- I don’t want to say bigger -- but it was equal with the record. It wasn’t like the record was a big hit on its own. The video really did something to it that elevated it into the people’s consciousness. That was my admission into the club."

X has recently stepped into the film industry, making his directorial debut with June's Superfly remake, starring Trevor Jackson, Jason Mitchell and Michael K. Williams. But the director claims the transition from videos to movies wasn't a difficult one. "Truly the biggest difference is timing. You’re shooting the movie over the course of 15, 30, 40 days -- depending on the production," he says. "It takes a lot of time to set it up, to shoot it and to edit. One of my mentors told me, “It’s not that complex, X. You point the camera at the person and shoot!”

While he continues to explore new projects like movies and Mister Tachyon -- his new sci-fi series on Viceland that premiered this July -- Director X's heart remains with music videos. Below, the auteur looks back of some of the memorable highlights throughout his career, like when two star-crossed superstars met for the first time on one of his sets, and the biggest thing that still kills him about Iggy Azalea's "Fancy" video.

2000: Mystikal, “Danger (Been So Long)” featuring Nivea

The director of photography for that video, Claudio Miranda, ended up winning an Academy Award for Life of Pi, so there’s that! The vibe on set was cool and we had a lot to do: one day on the desert and then off to go shoot at the next location. To me, it was a regular shoot. I don’t remember how I came up with that face-licking scene [towards the end of the video]. We were just being silly.

2001: Usher, “U Got It Bad”

Most people would say there’s a difference between working with R&B singers and rappers, but there isn’t. I just do me. This one was a little more personal. I was young and was kind of venting through my own life experience through the song. Usher and I were around the same age, and it was just one of those [videos] that really clicked. I think there was something special about that video, having a really young director with a really young artist making this thing happen together.

It wasn’t that hard to shoot [the final dance scene in the rain]. I think Usher pulled something, though. When he jumps up and grabs the pole, he injured himself. We were all injured at that shoot. I burned my hand because I tripped and grabbed onto a light, I also hurt my ankle. We all got hurt somehow doing that video! But it’s all for the art. [Laughs.]

2002: Nelly, “Hot In Herre”

We definitely gelled the lights to make that blue tint, but it wasn’t a juxtaposition with the song or anything. I was just doing whatever I do, you know? Cedric the Entertainer and Nelly are from the same hometown, so it was Nelly’s idea [to put him in the video]. They had that hometown love between the two of them and it was a funny moment. It was cool working with Nelly; he’s always been a good person. And it wasn’t that sweaty on set -- that was just some movie magic right there!

2002: Sean Paul's “Gimme The Light”

It was great being part of such a big moment in Sean Paul’s career, just with me being a West Indian kid from Toronto. You know, when we did the “Gimme The Light” video, it had been on the radio for a long time. In markets that listen to reggae music, “Gimme The Light” was already a big record, but no one was really remixing it. But then we did the video, and the rest of the world saw the [Caribbean] culture. That was the thing that we were always doing with Sean Paul: It was more than just highlighting Sean Paul as an artist. It was the culture of the West Indies that we were bringing forth.

So “Gimme The Light” came out, and you got to see the young people and the way they danced. But it looked like a big hip-hop video, with the lights and the set. People really got it, and you had this huge reggae explosion where all these reggae artists were back on TV and their music was getting played. It was that moment in time, and it was exciting.

2003: Sean Paul, "I'm Still In Love With You" featuring Sasha

This video was released a little bit deeper into when Sean Paul became Sean Paul. But it was yet another example of what music videos can do. "I'm Still In Love With You" may have been the third or fourth video [I did with him]. It was pretty established that Sean Paul was a major artist at that point.

I don’t know if I miss that time [when dancehall artists were getting into the mainstream market] as much as I can appreciate it. It was great to be part of that catalyst that brought it back around. My whole team, we were all kids from West Indian backgrounds. Either first-generation, or born in the West Indies and moved to America and Canada. So it was more than just a job. It felt like we were doing something for our culture.

2004: Kanye West, "The New Workout Plan"

That video and the infomercial idea was all Kanye [West]. He’s a funny guy and he loves comedy. It was a very silly day [on set], in the best possible way! [laughs] All the cameos [John Legend, GLC, Tracee Ellis Ross, Fonzworth Bentley, Anna Nicole Smith] made watching the video an event. Back in those days when they played videos on television, you’d sit in your room and see these cameo appearances, and it made the video feel like a bigger thing as a fan or the audience. It was exciting.

2005: Rihanna, "Pon de Replay"

We gave the dancers something to do [to make the nightclub setting look interesting]. You can make things interesting either by changing location or changing the action. Someone sitting and then standing up is a change. It just needs to feel like something is progressing, and that’s the key element. I felt Rihanna’s star quality on set, and I’ll tell you when I really knew it. When we shot her performance -- she was wearing a turquoise dress -- and she was just singing the song, I was watching her and was like, “Oh I see what this is.” When I saw that happen, I knew this was something special. She had real star power then and who knew she'd become this big?

I actually brought her to Toronto to do that video. Her video was shot at my hometown! I think her and Drake met around that time. When he presented her that [Video Vanguard] award at the [2016 MTV Video Music Awards] and did that speech, he said something about first meeting her at this restaurant where he was the DJ or singing there. She was out there doing her thing and they bumped into each other. They were still teenagers then.

2012: Drake, "HYFR"

This is around the time when I began to do the vertical opening instead of my signature horizontal one. Even until now, people still do that opening I used to do. You see it all the damn time. Very few people know that came from me and my camp. My editor Cat Brown came up with that at the time, and people liked it. It’s kind of like dance: One person does a dance step and then everyone else does it. Then you’re like, “No! Jimmy from the Bronx came up with that!" [Laughs.] But it’s gone now! When I saw it was getting away from me and that it was no longer an indication for what I was doing, just more so people doing it for their videos, that’s when I knew I needed to change it. That’s when I switched up the direction of where the opening was going, even though that was my signature.

It wasn’t easy shooting in a synagogue, especially getting the permission. But we got it, thankfully. In the edit, they were very specific. There couldn’t be any swear words -- at least you don’t see [Drake] swearing in the synagogue. All that happened at the actual bar mitzvah. Drake and I’s chemistry maybe comes from us being from the same hometown -- and we go so far back, just knowing the same people. It’s just very comfortable. There’s something between us that doesn’t have to be explained, and even now with Karena [Evans, director of Drake's videos for "God's Plan," "Nice for What" and "I'm Upset"], it still feels like it’s just family.

2014: Iggy Azalea featuring Charli XCX, "Fancy"

Iggy [Azalea] is very involved when she does these types of projects, especially on the fashion side. So her and her stylist were on that from the beginning, and there were no games being played. The time to shoot the video wasn’t [very long], but she had a workforce around her who was just as dedicated as she was to make sure everything looked right. They just handled it.

If I could go back in time actually, what I would have done is -- when she goes walking down the hallway in the yellow outfit in that third verse, that should’ve been the first thing you saw. It should’ve been her walking down the hall, and then cut to the classroom, so I kind of messed it up. It would’ve made for a better effect, because we first saw her pick the outfit in her room. So then you’d see her feet and the camera would pan up to her outfit and you’d see her walking. My mistake! While we were shooting it, we knew something wasn’t right, but we couldn’t quite figure out what it was. You ever look back and say, “Oh, I wish I could change that?” A lot of times during shooting, I wouldn’t kill [a scene]. But I would go back to Iggy Azalea’s video shoot and say, “Hey! Make this the first verse!”

2015: Drake, "Hotline Bling"

That was a big, big set, and was very complex. Those lighting effects are happening in the camera. So shooting that video was not easy, and wasn’t a simple production to pull off or build. We shot the set with the stairs, and then we had to pull those out to fit the other set with the two big walls that kind of spread out, which was a forced-perspective set. It was a giant production. And those pastel colors just felt right. [“Hotline Bling”] is a light-hearted song, so it needed a light-hearted approach.

The [Sean Paul dance reference in the video] was Drake’s idea. He was like, “I want to do the ‘Gimme The Light’ thing!” That just speaks to how far the video has come. Like who knew that was going to be a moment! You gotta remember, Drake was a teenager when “Gimme The Light” came out, and those kids in the video were kids that [choreographer Tanisha Scott] knows. This was when [Toronto] was beginning to change. The kids who you went to school with are now dancing in music videos. This is a worldwide hit and your friend is in the video! This was not normal for Toronto. Maybe in New York or Los Angeles where they were doing this shit, but not Toronto.

I didn’t think “Hotline Bling” was going to spark so many memes. When we did the video, I thought it was going to be something big for our culture and for hip-hop. Then it just exploded past that, and went into this whole ‘nother territory.

2016: Rihanna featuring Drake, "Work"

There was a reason why we brought it to Toronto, to have that Caribbean authenticity. We wouldn’t have to explain to anybody what’s going on. When Rihanna goes up to that guy and dances with him in the video -- that wasn’t planned. She just did it. And he was one of the kids in the “Pon De Replay” video! It was very much a full-circle experience, where these kids who were in her very first video are now back on set with her. Toronto is a “big” small city. If you’re on the scene, everyone knows each other. So it was great to see those little moments happen. And it wasn’t easy shooting in the dark. We were right on the fine line, that’s for sure.

Rihanna has matured a lot since I first worked with her. I remember when she was a little prankster at 17 and was a charming kid. Now she’s very regal, very grown. She’s now a strong woman.