Songfacts®:

• Usher wrote "My Way" with the track's producers, Jermaine Dupri and Manuel Seal. Usher wanted to do his own version of Frank Sinatra's signature song, "My Way" to signify his newfound independence; his debut album, released in 1994 when he was 15, was conceptualized by Puff Daddy, so Usher was just a performer. That changed for his second album when he had a hand in the songwriting and took control of his image.
  
  "'My Way' started because I found out about Frank Sinatra," he said in a documentary about the making of the album. "His voice is amazing. I found this song 'My Way,' and I thought, 'That's how I feel right now.' So I brought this idea to JD. My version of it was really inspired by Frank Sinatra. His version of it was more hip-hop: She likes it my way. She keeps running back to see me do it my way. It's like kicking your game, being extremely confident."
• "My Way" was the third single from the album, following "You Make Me Wanna" and "Nice & Slow." All of them were huge hits and helped the album sell over 7 million copies. Usher was just 18 when the album was released but had logged enough time in the industry to have some maturity. He handled the fame like a boss and became an even bigger star in the '00s, when he landed seven more #1 hits.
• In the music video, Usher is at some kind of junkyard carnival when Tyrese comes by with his crew and they get in a West Side Story style dance fight. It was directed by Hype Williams, who also shot the video for "Nice & Slow."
• Jermaine Dupri did the ad-libs on this track and the rap in the middle. Early in his career, Dupri didn't like putting his own vocals on the tracks he produced, but by this point he was comfortable with it. Another super-producer of this era, Timbaland, also did this a lot.
• Usher wears a fedora in the music video and on the single art as a nod to Frank Sinatra. Another call-out to Sinatra is at the beginning of the video where some big-band-style music - Sinatra's specialty - plays.