The Interesting Story of Kyle McMahon

The Interesting Story of Kyle McMahon

By Courtney Lane

May 5, 2020

Kyle Mcmahon joined iHeart Radio last November, originally starting on 92.9 TOM-FM and 94.7 WDSD. He created Pop Culture Weekly, a weekly podcast covering movies, music and tv and which features celebrity interviews. A little over a year later, Kyle is focused solely on Pop Culture Weekly, which is promoted on iHeart Radio stations across the country, including Pop Culture Minute, a one minute feature which runs three times daily.

Previous to iHeart, McMahon had been all over the place signing a record deal right out of high school, telling his story to the world from Oprah’s stage and creating a platform on his website to allow others to tell their stories. From Warner Brothers to Oprah to the Oscars, McMahon has had quite a ride.

We spoke via Zoom just after his birthday to discuss his career and moving to iHeart Radio. I start about by asking about what a birthday in quarantine is like.

Kyle McMahon: “Yeah May 1st was my birthday! It was weird because I couldn’t go out and celebrate like we normally would, but one of my friends rounded up my family and did a drive by surprise parade! It was so cool and I was totally shocked. I was literally in bed and my friend asked me to come outside to get something. I was thinking, “Ugh I just laid down to take a nap.” And here she had this whole line of cars down the street waiting for me to come out. I’m a Taurus, by the way, if that wasn’t obvious.” <laughs>

Courtney: “I can see that. “<laughs>


Courtney: “You have an interesting story before you came to iHeart. Tell me about that.”

Kyle: “Interesting is a good word. I always say weird. <laughs> I’ve had a weird life. My biological father essentially abandoned me and my mom when she was pregnant with me. Even so, despite that, I had a great life growing up. My family is incredible. And my Mom, she never had me wanting for anything. She worked her butt off making sure I went to a great school. Then, she met my Dad when I was probably 8? They eventually married, and he joined the Navy.“


McMahon lights up as he talks about his Mom and stepfather, who he calls Dad. Despite being “fatherless” by biology, his Dad remained a constant. He explains why one doesn’t necessarily substitute for the other.


Kyle: “I definitely struggled with wondering why my father chose to leave. There were some really, really bad times that stemmed from that abandonment. I questioned so many things including my self worth. It really does effect everything. But I eventually came to learn that it had nothing to do with me. His choices were just that: his. I can’t explain why people do horrible things. And I no longer will allow myself to be tortured by someone else choices.

Anyway, I was always into art and music and performing. My mom always encouraged me to use art as an outlet…and I did. She made sure - well, tried to make sure - I was well rounded by involving me in sports, but my mind was always on creating. I played sports. Well, at least I showed up to sports. <laughs> I remember being in the outfield daydreaming about performing or writing or whatever. I even used to do a radio show with my friend with a little tape recorder.” <laughs>

Courtney: “A foretelling.”

Kyle: “Definitely. So fast forward to high school and soon after I signed a development deal with Warner Brothers. That eventually turned into an album deal with 111 Warner. It was Brad Fischetti from LFO who signed me. I was recording all over the country. Los Angeles, Orlando, Atlanta, New York City, Boston. I worked with some of my favorite producers. Including my good friend Monte Pittman, who works very closely with Madonna.”

Courtney: “But then your Dad got deployed?”

Kyle: “Yes, so then my Dad got deployed overseas and I didn’t want to be traveling like that with my Mom home while her husband is overseas and my Grandmother was beating cancer at the time. So, I put music to the side, temporarily.”


McMahon released a cover of I Don’t Wanna Fight, the 1993 Tina Turner hit for the album What’s Love? A Tribute To Tina Turner. Snippets of a few original songs, for his debut Warner album, remain on an old MySpace Music page.


Courtney: “How did Oprah come into the picture?”

Kyle: “I don’t remember the exact specifics, but I had written this song called A Letter 2 My Younger Self, which wasn’t like a pop song. It would never be a single. It was just a song I wrote for myself as a literal letter to my younger self about my father choosing to leave. I get a call from one of the Harpo Producers and he said Oprah was doing a new show on OWN called Oprah’s Lifeclass and they wanted to talk to me about my biological father leaving for an episode they were doing on fatherlessness. I ended up going to Chicago like 6 times in just a few month period. To meet with them, to do pre-interviews, the show. Well that one show turned into five I think. I think it was five episodes. Momma O herself just decided in the middle of the first episode that it was now going to be a two parter. Eventually that two parter turned into multiple episodes.”

Courtney: “What was that like for you telling your story to Oprah?”

Kyle: “It was surreal. Miss Iyanla Vanzant was the “life coach” on the show and she is incredible. As Oprah and Iyanla introduced me & showed my story on a video in Harpo Studios with the world watching, I got really scared. Then something just came over me and said “You’re here to heal. Tell your truth.” So, that’s what I did. And of course, I cried on national television…again. But it totally freed me. It truly did. It totally freed me.”


Oprah’s Lifeclass: Fatherless Sons was a hit, becoming the 2nd most viewed program on OWN at that time. It wasn’t just a success for OWN, it was a success for McMahon, both personally and professionally.


Courtney: “It won an Emmy right?”

Kyle: “It did! It won an Emmy and the separate PSA they did (that) I was featured in won some sort of award for PSA’s too. Oprah, Iyanla, doing those shows totally changed my life.”


Oprah’s Lifeclass won the Gold ProMAX award for TV: Video Presentation / News Program. It also won the NAACP Award for outstanding television. #TeamKyle trended on Twitter during one of the re-broadcasts. He released a self directed music video for the song A Letter 2 My Younger Self (Fatherless Sons) to coincide with the first Oprah’s Lifeclass episode. The music video, which shows the story of a young couple arguing after she gets a positive pregnancy test is intercut with scenes of McMahon and a child representing a young McMahon tearing apart letters they’ve written about the feelings that come with parental abandonment.

So, “totally changed my life” is an understatement.


Courtney: “I bet. Then what happened?”

Kyle: “Then from that I got a gig writing self improvement articles for Millennials on the OWN section of Huffington Post. I had a tiny part in the film Selma. I went down to Georgia. It was directed by the incredible Ava Duvernay. She’s such an unbelievably talented visionary. Then Selma won an Oscar.”

Courtney: “That’s cool!”

Kyle: “Yeah, I joke with people that I’ve got an Oscar and an Emmy, now I just need a Tony and a Grammy.” <laughs>

Courtney: <laughs>

Kyle: “I mean, I’m joking about that because I personally didn’t win anything. <laughs> But yeah it really did change my life. And then it was so cool because I got a call to work with the Obama administration on an initiative they launched called My Brothers Keeper, which helped give outlets and guidance to at risk fatherless youth. (It’s) Such an awesome program. And that turned into the United Nations Youth Assembly which I’m still involved in.”


United Nations Youth Assembly is a program through United Nations in Washington DC that brings together people 40 and under from around the world to brain storm on solving global issues. Through classes, lectures and breakout sessions, the Assembly then goes back into their own regions spreading the lessons they’ve learned to create positive change.


Kyle: “And for Father’s Day, probably, 3 years ago now? My Dad officially adopted me!”

Courtney: “Oh wow that’s such a great ending to that chapter!”

Kyle: “It really is. He was always willing to adopt me, but I hadn’t been ready. For Father’s Day a few years back, in his card I wrote that I was ready. I wanted him to adopt me. And he did. He was so happy, I was so happy. We went to Family Court together to make it official. It is such a special moment to me.”


McMahon begins tearing up as he speaks about the adoption.


Kyle: “I always say I had searched my whole life for my father, and my Dad was right there. But honestly, I had to go through that search and that pain to get where I am today. I learned so much. And my Dad totally understood. He wasn’t angry. He wasn’t angry that I did the shows. He understood.”

Courtney: “You’re going to make me cry, now.”

Kyle: “See, it just happens. At least we’re not on national TV right now.” <laughs>

Courtney: <laughs>


I shifted the conversation to something a bit lighter. McMahon had recently toured with multi-platinum pop group, LFO. With Rich Cronin having passed at 36 from Leukemia in 2010, Brad Fischetti and Devin Lima hit the road for the 2017 tour Rich In Love. McMahon joined the group on an 18 city trek, taking the stage each night in the middle of LFO’s set to sing various boy band favorites, most often Backstreet Boys I Want It That Way. He would also join in with the group on various songs from LFO’s own hit filled catalogue.


Courtney: So you also recently finished a tour with LFO?

Kyle: Yeah, how crazy is that? I was a huge fan of boy bands growing up. I mean, I still am. Because I love pop music and because I wanted to be in one. <laughs>. And it was ironic that Brad (from LFO) signed me to 111 (Warner) after LFO went on hiatus. They had done a short run reunion tour, which I met up with them for a bunch of dates, but then Rich got sick. He passed in 2010 and I thought LFO was done.

Courtney: How did the Rich In Love tour happen?

Kyle: Well, I was at Hershey Stadium in Pennsylvania covering the Mix Tape Tour for my show and 98 Degrees came out to do their set. They did this one section where it was like a medley of some of the great boy band songs and I started videoing it. They started the chords to Summer Girls & I was freaking out. I immediately sent it to Brad, who reached out to the guys in 98 to thank them. They ended up inviting him and Devin to their Coney Island show to do a surprise performance. I went with them as sort of a handler. The crowd went absolutely insane.

There was a booking agent in the crowd who witnessed 10,000 people just go nuts for LFO and he contacted the guys to talk them into going on the road. And they were kind enough to invite me with them. I honestly had one of the best times of my life on that tour. It was a whirlwind of interviews, appearances, shower, get to the venue, travel to the next city and repeat. It was exhausting but I loved every single second of it."


Sadly, just as the second leg of the Rich In Love Tour was to be announced in October 2017, Devin Lima was diagnosed with stage four adrenal cancer. He passed away 13 months later in November 2018. McMahon was set to join Fischetti on select dates on the O-Town Y2K Tour before COVID-19 forced the dates to be rescheduled for 2021.

Besides part time boy band member, McMahon has been a correspondent with PBS on their two highest rated programs, National Memorial Day Concert and A Capitol Fourth. I ask how these came about.


Kyle: “So my friend Melinda works with them at PBS and she asked if I wanted to come down and cover the (A Capitol Fourth) show. I was like, ‘Ummmm, yes!’. So I went down to Washington DC and it’s so crazy. Capitol Concerts, who put on the show for PBS, is a top notch production company. It’s on the West Lawn of the U.S. Capitol. There’s this big glorious stage. These satellite stages. I honestly teared up. And I guess they liked what I did because I’ve been going back every year since. I really love working with them.”

Courtney: “Then Christa Cooper saw your videos right?”

Kyle: “Yes, and the opportunity with iHeart came up and I was all in. Obviously, I started with TOM & (W)DSD, but my goal was always to do a pop culture show. I had experience doing videos and a podcast on my own.”


A few years prior, McMahon had created Kyle2U, a podcast coinciding with his website, whose motto is ‘Transform Your Life’. The show featured numerous celebrities, thought leaders and newsmakers, as well as simply frank discussions on issues like race, transgenderism and even gun control. That experience helped him to dive right in to his own show with iHeart.

I asked McMahon how Pop Culture Weekly started.


Kyle: “Well, I had started this site years ago called Pop Culture Whore and it was pretty popular for awhile. It got so popular at one point other people were writing articles for the site too. I’m a huge movie buff. I love music. I love storytelling no matter if the medium is TV or a song or a movie or whatever. I’ve always just loved pop culture. I mean I use to record every single episode of all my favorite shows as a kid. I’d record them and then meticulously catalogue them with an episode synopsis and everything. With the help of the internet of course. So one of the things I could talk about forever is pop culture. So I started Pop Culture Weekly. And people seem to really enjoy the show. It’s not celebrity focused. Meaning like, we don’t cover celebrity gossip. We cover their work.


The show is now promoted across iHeart Radios one thousand plus stations. Guests have included Oscar nominees like the cast of Roma, to Grammy winners like Michael Bolton to Top 40 stars like Lauv to spiritual icon Deepak Chopra, to the cast of Servant, including Harry Potter’s own Ron Weasley, Rupert Grint.

McMahon, a self described huge Harry Potter fan, could talk for hours about the Harry Potter franchise.


Kyle: “Yes that is one of my favorite interviews. I freakin love Harry Potter and I love Ron Weasley and I love Rupert Grint. And he’s on Servant on Apple TV+, which is from M Night Shyamalan, one of my favorite directors. It was just a really cool moment for me. Hufflepuff forever!” <laughs>

Courtney: “So what’s next for you?”

Kyle: “I mean, I always have a 5 year plan, but that plan has almost always been superseded by actual life taking me on wild turns that have made it better than I imagined. I didn’t think I’d be at iHeart two years ago, but on my five year plan back then was for me to be on the radio. And then it happened.

But who knows? Maybe Pop Culture Weekly the show? We’ll see where this takes me. Where life takes me. I also never want to give away my cards. I’ve got to have that pa…pa…pa poker face. Pa…pa…poker face.” <laughs>


How else do you wind down an interview with a guy who has a show called Pop Culture Weekly then with a random reference to Lady Gaga’s 2008 hit? There really isn’t a better ending, so with that, we bid farewell for now. We’ll certainly be hearing from McMahon very soon in one form or another - or all of them at once.