Chatting with host and Billboard co-director of charts Gary Trust, Hilton traces his career path, which was sparked in large part by his first on-stage appearance with an iconic diva at age six. (The intro music of the podcast reveals which one.) Hilton then made his name as perhaps the preeminent celebrity blogger, and not always in the most flattering light, thanks to his penchant for over-the-top snark. Now 38, and a father of two, Hilton owns his past. "I have tons of regrets," he says. "I wish I [could've done] so many things differently, and I actually would. A lot of people say, 'I wouldn't do anything differently, because it all led me to where I am.' But, it truly makes me … more than just sad. I feel … shame and regret that, along the way, I purposefully caused pain and hurt to other people, for attention and page views.
"With age comes confidence," Hilton continues. "I'm confident now that I still could have, and would have, been successful without having to do all that. But, when I was younger, I didn't know better. There's that great quote from Maya Angelou: 'When you know better, you do better.'
"There just came a point where I said, 'You know what? People are viewing me in a certain way, and that's not who I am. That's not who I am in my heart and I need to stop hiding behind this character that I created and show the world the real me.' And that's what I've been trying to do the last few years."
The affable Hilton also dishes on his relationships with artists including Madonna, Justin Bieber, Jennifer Lopez and Taylor Swift, the latter of whom recently eschewed his advice, and earned another top 10 Billboard Hot 100 hit as a result. "Right after the 'Bad Blood' video [last year], I told her, 'This needs to be the end of this  album cycle. Take a break and then release a new album in the fourth quarter of 2016.' Then, she goes and releases three more singles [including the No. 5 smash 'Wildest Dreams']! She would've left people wanting more." Ultimately, Hilton defers to Swift's perhaps unrivaled business sense: "There is no smarter musician in the game right now."
A sampling of previous episodes:
Dave Cobb & Jed Hill on Americana Music / SiriusXM's Kid Kelly / Original MTV VJ Martha Quinn / RCA's Joe Riccitelli on Britney Spears & Justin Timberlake / Mike Curb / Hit Songs Deconstructed on Drake & Selena Gomez / Fred Bronson / Chart Beat Founder Paul Grein
Enjoy the entire latest Chart Beat Podcast and check back for more upcoming episodes with label execs, radio programmers and personalities, songwriters, producers and more. And, to receive every episode automatically in your inbox, subscribe to (and rate) the Billboard Chart Beat Podcast on iTunes!