On this episode of The Hollywood Outsider podcast, it's that time of year: Valentine's Day. A time to reflect on love...BAD LOVE! Or missed opportunities for love! We are heading down memory lane to discuss those TV and movie couples who either should have ended up together but didn't, and shouldn't have ended up together but did. In other words, these are the mistakes.

Then we discuss losing Catherine O'Hara, review Whistle, in theaters now, and discuss recommendations such as The Wrecking Crew on Prime and Roofman on Paramount+.

• (0:00 – 1:20:46) Couples in TV and Movies That Should or Should Not Have Gotten Together
• (1:20:47 – 1:37:04) Catherine O'Hara | Spoiler-free Review: Whistle | Recommendations: The Wrecking Crew, Roofman
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On this episode of The Hollywood Outsider podcast, we are kicking things off with a breakdown and discussion on Oscars 2026, that's right, the 98th Academy Awards nominations are here! From what should win to what seems to be the actual frontrunner in all of the major categories. Was One Battle After Another the best of the year? Did Sinners deserve a record 16 nominations? Should Timothée Chalamet finally receive his first Oscar?

The 98th Annual Academy Awards will air Sunday, March 15, 2026, at 7 p.m. EDT (4 p.m. PDT) on ABC and Hulu.

Visit TheHollywoodOutsider.com for a full list of nominees

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On this episode of The Hollywood Outsider podcast, we're breaking down everything that's getting us excited around TV with our 2026 TV Preview Extravaganza! We talk about 30 new shows coming to both streaming and networks this year plus 15 returning shows all with their respective release date and a brief synopsis. New shows such as Vanished, Steal, The Burbs, Strip Law, Marshalls, CIA, and more as well as returning gems like Scrubs, Shrinking, One Piece, Hijack, The Pitt, The Boys, The Bear and so many more. Last year was full of highlights, but 2026 is looking even more exciting. Enjoy our 2026 TV Preview Extravaganza! What 2026 TV shows are you most looking forward to?

• Kennedy is out and Filoni is in at Lucas Film
• Netflix updates to all cash deal to buy Warner Brothers and HBO
• The 2026 TV Preview Extravaganza!
• Star Trek: Starfleet Academy thoughts
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On this episode of The Hollywood Outsider podcast, we're breaking down everything that's getting us excited in film with our 2026 Movie Preview Extravaganza! We talk about all the big movies coming to theaters and streaming this year with their respective release date and a brief synopsis. Blockbusters such as Supergirl, Digger, Scream 7, Moana, Star Wars: The Mandalorian and Grogu, Avengers: Doomsday, Dune: Part Three, Project Hail Mary, The Devil Wears Prada 2, The Odyssey, Toy Story 5, as well as plenty of smaller films like Ready or Not 2, Obsession, Send Help, and so many more. Last year was full of highlights, but 2026 is looking even more exciting. Enjoy our 2026 Movie Preview Extravaganza!

What 2026 movie releases are you most looking forward to?

• 2026 Movie Preview Extravaganza!
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• Please support The Hollywood Outsider and gain immediate access to bonus content, including Patreon exclusive podcast content like our Bad Movie Night by visiting Patreon.com/ TheHollywoodOutsider
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These are the only awards that really matter, the 2026 HO Awards! On this episode of The Hollywood Outsider podcast, we are breaking down our 2026 awards for both film and television. If you haven't listened to our HO Awards for movies and TV before, we do ours a bit different, for example our "actor" category covers all genders, we do not separate it. For TV: network, cable, and streaming all count, it just has to have had at least 3 new episodes in 2025. For movies, theatrical, VOD, and streaming are all eligible.

If you want to follow along, the categories are below, so let us know what your picks are on our social media channels. What will take our awards? Wake Up Dead Man, The Pitt, Stranger Things, Reacher, Pluribus, F1: The Movie, Thunderbolts, Bugonia, Adolescence, Severance, Weapons, Sinners, The Housemaid, or something else? Each of us will award our winners in each category, and at the end, we'll combine ours with listener picks to determine what was the HO TV series and Movie of the Year!

Take a listen to the 2026 HO Awards for TV and Film!

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• (0:00 – 15:22) Opening | Best Movie or TV Experience, Most Impactful News Story
• (15:23 – 59:43) Television Awards
• (59:44 – 1:56:35) Film Awards
• (1:56:36 - 2:11:08) Listener Top 10 | HO TV Series and HO Movie of the Year
• Listen to our podcast, Inspired By A True Story, now available in your favorite podcast feed!
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• Be wary of potential mild spoilers for 2024 films and TV series

TV Award Categories

• Best Special Effects and/or Stunts on TV
• Best Villain or Badass
• Best Supporting Actor
• Best Actor
• Most Disappointing Series
• Best Specific Moment on TV
• The Justin Macumber Award: Little-seen or discussed TV series that just completely won you over and you hope more people find it in the new year. Named after the late Justin Macumber.
• The Top 10

Movie Award Categories

• Best Physical Effects or Stunts
• Best Use of CGI in Film
• Best Villain or Badass
• Best Supporting Actor
• Best Actor
• Most Disappointing Series
• Best Specific Moment in Film
• The Justin Macumber Award: Little-seen or discussed film that just completely won you over and you hope more people find it in the new year. Named after the late Justin Macumber.
• The Top 10

On this episode of The Hollywood Outsider podcast, it is time to say goodbye to one of our favorite TV shows of this century with our Stranger Things Season 5 and Series Finale spoiler review and wrap-up! We venture through each and every character's arc, hitting highs and lows, debating Will's monologue and the reaction it caused, the choice to focus on Holly this season, the finale and repercussions, and so much more.

Hawkins, Indiana will never be the same. So let's head into this special podcast and spend one last adventure with Mike, Will, Lucas, Dustin, Eleven, Max, Hopper, Joyce, Nancy, Jonathan, Steve, and the 46 other characters we met along the road. Goodbye, Stranger Things!

• • Stranger Things Season 5
  • The Finale and Season Revelations
  • Each Character's Journey
  • Will's Monologue, Vecna's Plan, Eleven's Choice
  • Click here for more info on our 2026 Alaskan Cruise!
  • Please support The Hollywood Outsider and gain immediate access to bonus content, including Patreon exclusive podcast content like our Bad Movie Night by visiting Patreon.com/ TheHollywoodOutsider

On this episode of The Hollywood Outsider podcast, it is time for our final episode of the year, and therefore it is time to say goodbye to 2025! We dive into a few of the biggest stories of the year - while shying away from all of that low-hanging political fruit - as well as recent news on director Rob Reiner that has impacted us all. The Warner Brothers and Netflix OR Paramount merger, watercooler TV makes a resurgence, K-Pop Demon Hunters, and even the impact of AI.

Then, we say cheers to the past 25 years in movie and TV by an entire section of our show dedicated to a few of the highlights and even - using AI - determining what truly is the best of the best when it comes to this quarter century. How accurate is it? Let's find out together.

It's a packed episode, and we appreciate all of your support, so we hope you enjoy. We will see you on the other side of 2026!

• (0:00 – 46:59) Goodbye 2025
• (47:00 – 1:20:06) Cheers to the Past 25 Years
• Click here for more info on our 2026 Alaskan Cruise!
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On this episode of The Hollywood Outsider podcast, we are at the quarter mark of this century and it is time to reflect. This is an introspective look back at our favorite movies and TV shows between 2000 and 2025, aka the past 25 years, with both narrowing our focus down to our favorites within this time frame, as well as listener Top 10s. This episode covers a lot of ground, so enjoy this discussion on the best movies and TV shows of the 2000s!

• (0:00 – 1:14:30) The Best Movies of the 2000s
• (1:14:31 – 2:08:37) The Best TV Shows of the 2000s
• Click here for more info on our 2026 Alaskan Cruise!
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On this episode of The Hollywood Outsider podcast, we are at the quarter mark of this century and it is time to reflect. Therefore we are continuing our series that we began earlier this years by discussing the best holiday or Christmas movies of the past 25 years. The important distinction here, is that these are the best movies that we watch at this time of year to get us in the holiday spirit, so they are not necessarily Christmas movies. Lord of the Rings, Harry Potter, Hateful Eight - they all are just as relevant as Elf or 8-Bit Christmas. So sit back, grab some mistletoe, and lets debate the best holiday movies of the 2000s!

Click here for info on our 2026 Alaskan Cruise!

• The Best Holiday or Christmas Movies of the Past 25 Years
• Please support The Hollywood Outsider and gain immediate access to bonus content, including Patreon exclusive podcast content like our Bad Movie Night by visiting Patreon.com/ TheHollywoodOutsider
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Every year, we love to celebrate the holiday season with our listeners, and there is no better way to do that than with our 2025 Holiday Special!

It all started 10 years ago with a random idea: we were big fans of holiday specials, yet podcasts seemed to skip over the idea completely. Therefore, we decided we can do whatever we want here at The Hollywood Outsider, so let's create our own tradition and the Annual Holiday Special was born!

Every year we rekindle the past (and occasionally add a little something new), assembling some of the best moments from our hosts for the most fantastic holiday special ever! Debating what constitutes a Christmas movie and specials we love, what makes for a great Christmas movie, Christmas cliches, and even our Holiday Spirit Movie Battle Royale!

That's not all, oh no. The Christmas spirit kicks into overdrive as we open up and share our personal memories of the holiday season, stories that remind us of Christmas. And no holiday special would be complete without a visit from the big man himself, so get ready for as much St. Nick as legally allowed as Santa Claus drops by the studio to tell us just how naughty or nice we are, all throughout the episode!

With a special game from Amanda, Santa in his sleigh, John's obsession with puppets, Troy's intriguing selection of Holiday Spirit films, Scott's first Christmas Poem, Bad Santa, and a lot of fun for everyone – This is the one podcast you don't want to miss this holiday season!