Will Smith sits across from talk show host Charlie Rose. His pointer finger hovers just above his cupid’s bow as he continues. “Fear of fear. I hate being scared to do something.” The interview is from 2002, but the mantra Smith speaks about could just as easily have tumbled out of his mouth today. The rapper, actor, comedian and — most recently, YouTuber — has turned his philosophy of life into a sort of tagline, a north star that resonates in everything from his films to vlogs on facing his biggest fears.

Smith will once again prove his fearlessness at the Grand Canyon during a live-streamed “helibungee” birthday stunt. It is exactly what it sounds like: bungee-jumping out of a helicopter. Smith may be there to prove his own courage, but his jump signifies something bigger than him. It’s the melding of old-school Hollywood with online celebrity in the era of YouTube.

The story behind Smith’s jump is a modern tale if there ever was one. It started with YouTube channel Yes Theory, a group of three earnest young men who enthusiastically embrace the idea of stepping outside of your comfort zone. The trio issued a challenge to Smith in February, daring him to join them in a jump. “For as long as we can remember, Will Smith has been a hero of ours,” explains one Yes Theory member, Ammar Kandil, in the challenge video. The group grew up on Smith’s work, from Fresh Prince to Men in Black and The Pursuit of Happyness. “But to us, he isn’t just another actor. He’s an ambassador of what we believe in, the Yes Theory. Part of what living by the Yes Theory means is realizing that if we want to create a better world together, we have to chose love over fear. And fear is a subject that Will Smith tackles on the daily.”

Little more than a week later, Smith responded with a video of his own. Challenge accepted, it declared.

Smith’s turn to YouTube was puzzling for some, even ridiculed by others. He’s not the first celebrity to try his hand at vlogging. But Smith isn’t just another A-list actor. He was “the most powerful actor” in Hollywood at the height of his career, a star who oozes the kind of universal charisma and relatability that ensures fans across the spectrum will forever remember him as the Fresh Prince and Agent J, and not the guy who starred in those very bad David Ayer films. That sort of talent has translated into fame, fortune, and awards for Smith in the past. Now, it gives him the power to transcend traditional Hollywood and roll unimpeded with the new wave of online celebrity. Smith isn’t trying to bring TV to YouTube; he’s meeting creators on their level.

In a vlog explaining how he landed one of his most iconic roles, Smith tells his story interview-style to a camera. “Being famous and broke is a shitty combination, ‘cause you still famous,” he says. An animated version of Smith side-eyes a fan asking for an autograph while he speaks. “People recognize you, but they recognize you while you sitting next to them on the bus.” Smith’s natural charisma, along with the goofy visual interpretation to add levity to the story, turns the anecdote into something intimate. It places the viewer behind the scenes in a visual way.

Smith’s focus on YouTube speaks to the actor’s ability to adapt, even after a long and prosperous career. Hollywood and YouTube will only continue to get closer, and Smith’s adoption is another step toward that unification. It’s a beneficial move for both sides. Kandil says that there’s much to learn from Smith’s lessons, whether they’re about self-esteem or fighting depression. “I saw so many of my friends engaging with [these videos] because it was things they were going through themselves, but they didn’t really find a voice out there that could discuss it like Will did. He’s just a very loving man, and the way he projects love, and the way he puts out his message is very powerful, and it’s very uniting.”