How Entertainment Reporter Jake Hamilton’s Star-Studded Career Took Off

If you’ve seen interviews with your favorite actors and/or directors on YouTube or are in the Chicago area, you probably noticed a blonde-haired, well-manicured entertainment reporter exhibiting infectious excitement with his subjects. The Colgate commercial smile and Tom Cruise jumping on Oprah’s couch enthusiasm you get with Jake Hamilton are the real deal. 

The 33-year-old Houston native, fresh off snagging another three Emmy nominations last Tuesday (10 to date) and 100,000 YouTube subscribers on his channel “Jake’s Takes” in August, has succeeded in becoming one of the nation’s top show business journalists because of his undying love for film and his deep gratitude in having secured a seat at the table.

“I always tell people I get paid to be myself for a living. The excitement I have talking to [Forbes] about movies is the same excitement I have talking to Steven Spielberg or the same excitement I would have talking to a buddy of mine who said, ‘Dude, did you just see the new Dune trailer?’ This was my life growing up,” Hamilton, whose first Emmy nomination came at age 19 in 2007 and first win came in 2011 at age 23, told Forbes via Zoom video. “This was my obsession. This was the stuff I got excited about.”

The Fox 32 Chicago reporter has already racked up an unrivaled list of interviewees by Hollywood royalty standards. Just in the seven days leading up to his mid-September chat with Forbes, jake had interviewed Jennifer Aniston with Reese Witherspoon, Jake Gyllenhaal with Antoine Fuqua, Jessica Chastain, Andrew Garfield, the cast and writer (David Chase) of The Many Saints of Newark, and the cast of Midnight Mass along with show creator Mike Flanagan, plus Melissa McCarthy with Chris O’Dowd.

Jake’s confidence and fun-loving inquisitive nature make him a natural with delivering in big-get interviews. But what happens when the tables are turned and we ask him the questions?

“It’s terrifying because I’m now overthinking every single one of my answers because I know what I want out of someone whenever I talk to them,” said Hamilton, modestly. “I know sometimes I need soundbites and not sound meals and I know you want to engage someone and be interesting and now I’m overthinking not just what I’m saying, but how I’m saying it because I know what I would be looking for on the flip side of it. So, really weird situation to be on this side of it.”

Jake, who as a youngster would all but wear out DVDs watching director’s commentary and would beg the video store down the street for any spare promotional posters, didn’t simply wake up with a dream job one day, he began willing it into existence at a young age.

Hamilton first broke onto the entertainment beat at age 14 when he was presented with the opportunity to be a film critic for The Houston Chronicle. Jake wasn’t a fan of the critic at the time’s takes and wrote The Chronicle asking to pen some reviews of his own. He was soon given a once-in-a-lifetime opportunity for an early teen by Chronicle editor Syd Kearney. 

“Somehow they said yes and they brought me on as their cool, hip teen film critic for The Houston Chronicle at 14 and I thought that I was god’s gift to film criticism at the time,” Jake said. “I go back and I read some of my early reviews [from then] and I go, ‘Oh my god, I was such a brat,’ just reading some of my early stuff and it was so pretentious. … Someone once told me that if you don’t look back at your old stuff and cringe that means you’re not getting any better.”

After taking a broadcast journalism class in high school, Jake saw a more distinct path for himself in television after recognizing a lack of entertainment coverage on TV in Houston.

“After emailing every station in town for a year, over and over just copying and pasting the same email just over and over and over and over again, finally someone emailed back and said, ‘For the love of god, man. Yes. Here, come on review a film, we’ll see what happens,’” Hamilton said. “Someone dropped out or they were missing a segment and the rest is history. … I basically just annoyed my way into the [industry]. Ninety percent of everything I have in this industry is because I annoyed someone so they said, ‘Fine, here take it.'”

After college, Jake found himself doing freelance entertainment work for the Fox affiliate in Houston. The person who gave him that opportunity, Tom Doerr, later became the news director in Chicago and brought Jake out to the Windy City.

Currently in his eighth year with Fox Chicago, Jake has more than found his groove in getting the most out of his interviews, opening stars up with his passion for their craft, and leaving a lasting impression with both those in front of him and the audience at home.

Hamilton’s most meaningful and memorable interview came when he was scheduled to sit down with his hero, Tom Hanks, for the first time in Dallas in conjunction with the Larry Crowne (2011) junket. Aside from the sentimental connotation, Hanks had scaled back on regional interviews in the years prior. It was a huge get.

“He had been told in advance that I was a big fan and he kind of saved me for the end of the day and when I walked in the room he had someone tell me, ‘Jake, I’m sorry… Tom had to run. He couldn’t do it, couldn’t make it.’ I was a kid and I was trying to be professional, my heart sank,” Hamilton said.

“I thought I was literally going to start weeping and all of a sudden in the corner of the room I hear, ‘Is that Brad Pitt? No, that’s Jake Hamilton.’ He comes across the room, gives me a big bear hug, brings me over to where we’re going to do the interview and the first question I asked him I got a, which is sort of my barometer for whether or not an interview is good, I got a ‘Oh wow, that’s really good question, man.’ 

“It was the greatest feeling in the world. … That’s my favorite interview of all time. I remember walking away from that interview and thinking, ‘Remember this feeling, bottle this moment because you may not have a better professional moment than this.”

Jake has also gotten to converse with two of his other biggest influences, Harrison Ford and Quentin Tarantino. The latter of which took a liking to Jake and his “ReelBlend” podcast partners Sean O’Connell (CinemaBlend), and Kevin McCarthy (Fox 5, Washington DC).

The men of “ReelBlend” had each separately interviewed Quentin for junkets.

“Quentin Tarantino is a great interview if you’re a fan of film because he’s a fan of film and he recognizes that spark in someone else; you can almost physically see him light up and he’ll really start geeking out with you,” Jake said.

The podcast booked a 20-minute exclusive interview with Tarantino when he was doing press for Once Upon a Time in Hollywood (2019).

“We all clicked, it was a phenomenal conversation, he had familiarized himself with the podcast in advance to kind of know what he was getting into,” Jake said of the chat with the iconic director. “We had a fun interview looking back on his career and also it was nearing the 20th anniversary of Pulp Fiction, it just clicked.

“And he ended the interview in a very Hollywood way, which is a thing you hear all the time, ‘We really got to do this again some time. I really wish I had more time than 20 minutes; we really have to do this again.’ Which is just a thing you hear and it’s very nice when you hear that but you don’t always put that much stock into it. …

“In a weird serendipitous moment, myself and my co-host Kevin ran into Quentin in Los Angeles a few months later at the Four Seasons bar and we bumped into him and he said, ‘I really would love to talk to you guys again. I really wish we had more than 20 minutes. I’d love to have a great conversation.’

“We said, ‘Hey man, you have an open invitation to this podcast at any time, whenever you want to come on. Less than 48 hours later we get an email from his publicist saying, ‘Hey, heard you ran into Quentin. If you can get yourself to New York, he’d love to sit down with you and we said absolutely.”

The guys got themselves to New York and had Tarantino to themselves in a conference room for nearly three hours ahead of Oscars season for an unforgettable discussion on Quentin’s career, his favorite movie of the decade, and much more.

A few months later, the pandemic began ramping up. As Tarantino usually leaves a few years in between films, Hamilton and co. didn’t expect to hear from him any time in the near future.

It was soon announced that the filmmaker had a novelization of Once Upon a Time in Hollywood coming out and “ReelBlend” was pitched again. This time, there would be a different setting.

“What if you guys hosted a live episode of your podcast with him, in front of the live audience in New Beverly Cinema?” Tarantino’s rep inquired. Quentin owns the LA theater and wanted to host a big event for the book’s launch there.

“It was Tarantino’s idea to do that and it was one of the coolest experiences of my entire life, sitting next to me on a stage it was Quentin Tarantino on my right and then two of my best friends on my left … and we talked live for two hours and just talked movies,” Jake said.

“We talked his movies, we talked other people’s movies and we talked his past stuff and just hearing him tell stories about Reservoir Dogs and he actually had the actors enact what happened, what went wrong in the jewelry store.

“He actually had them act that scene out so they would have that frame of reference even though we never actually knew what happened, what went wrong in Reservoir Dogs, I tried to get it out of him but he wouldn’t [tell]. He just kept dropping these morsels … I tried to take in the moment, ‘What is happening?’”

One moment Jake didn’t have much trouble taking in, because it keeps popping up, is his viral exchange with Spider-Man himself Tom Holland ahead of Spider-Man: Far From Home, which serves as the first time Holland was asked about the multiverse and potentially being joined by the former big screen spideys. The actor’s telling response after Jake’s question at 2:40 in the video back in 2019 made the clip go viral.

“Going back and watching the video, and it’s been analyzed like on CSI, ‘Enhance, enhance…’ If you watch Tom Holland’s body language, he’s incredibly uncomfortable with me asking the question,” Hamilton said. “And then he ends up giving sort of the junket answer, ‘Oh yeah, that’d be really great, I have no control over it, I don’t know what’s going to happen but if it does end up coming true…

“As we already know, the multiverse is going to end up being a part of this new film, they’re bringing in villains from past Andrew Garfield and Toby Maguire films, but if it ends up that Toby and Andrew are in it, I would go as far as to say he knew at that time I asked that question.”

As a movie and MCU fan, Jake is curbing his own expectations for the next web-slinger installment, Spider-Man: No Way Home. He’s trained his mind not to anticipate past Spider-Men Garfield and Maguire being in the upcoming December release.

“I have convinced myself that they’re not because I don’t want to be disappointed because a movie was not something it was never meant to be,” Hamilton said. “I feel like if I hype myself up to see them in this movie, and then they’re not and then I go see the movie and I’m disappointed in the movie because of something that was never going to happen, that’s not fair to the movie.

Jake believes No Way Home will set up circumstances for the three Spideys to be in another film together down the road, and also shared some inside info… “I can confirm, exclusively for Forbes, that I am not in Spider-Man: No Way Home,” Jake revealed.

He was thankful the Holland bit took off because it helped the interest in his previous, more uncomfortable, viral video cool down where Samuel L. Jackson jokingly tried to get Hamilton to say the N-word while promoting Django Unchained at 13:55 in the clip. Jake wouldn’t take the bait and went on to conduct a strong interview. To his surprise, the clip blew up beyond belief with Jackson being vilified for seeming to pick on a young reporter.

“Howard Stern even spoke about it [during] his interview. Now granted, I was incredibly uncomfortable,” Jake said. “He’s yelling at me like that scene from Pulp Fiction, like, ‘I dare you, I double-dare you… Say what one more time.’ It was like he was screaming, but we ended up laughing about it.” Jackson still jokes about the exchange when running into Hamilton.

In addition to his two Emmys and YouTube’s prestigious Silver Play Button awarded for netting 100K-plus subscribers, Hamilton will be finding out if he’ll have more hardware for his trophy case at the 2021 Chicago/Midwest Emmys on November 20 after receiving one nomination for “Outstanding Achievement for Arts/Entertainment – Long Form Content” and two for “Outstanding Achievement for News Specialty Report/Series – Arts/Culture/Entertainment”. Jake regularly uploads interviews to his YouTube page and you can catch him Monday-Friday on Fox 32 in Chicago.