Welcome to Deep Trouble

Hello! I was hoping to save this welcome and introduction for early next year. No one would recommend you launch your “brand” (?) pivot a few weeks before Christmas. Well, I didn’t know Netflix would put out a documentary so full of lies and debunked information that it would send me into a rage; forcing me to write a 20,000 word piece.

A lot of new people have joined me since that post went up, so I’d love to introduce myself and Deep Trouble: I’m Ashley Ray, stand-up comedian, pop culture critic, podcast host and freelance writer. I used to write reviews for the A.V. Club and Vulture. You might be familiar with my Insecure or I May Destroy You reviews. Or my 90 Day Fiancé Universe Guide. I’ve interviewed people you love and written things you might’ve liked across the web.

Maybe you recognize me as a talking head on MSNBC, Hulu or Vice on topics ranging from polyamory to tv streaming? Or maybe you listened to my debut comedy album, Ice Cream Money? Or you listened to my podcast, TV, I Say! Where I interviewed your favorite comedians, actors and writers about the shows they make and love. That might even be how you subscribed to this newsletter and now you’re like, what the heck is this!

Well, I love TV. A lot. So much, I even started writing for TV shows over the last few years. If you listened to the pod, you might remember all those people who make TV saying things like “When I’m working on something, it’s so hard to watch other TV shows” and it turns out, they’re right. It’s so hard to watch so much TV and talk about it while you’re writing TV.

I stopped doing TV reviews back in 2020 to focus on writing my own work and TV I Say was a great way to yell about Chicago inaccuracies in The Bear, gossip about the Emmys and, again, to flirt with Jason Mantzoukas. But, a TV podcast and newsletter still require watching a lot of TV and you can only talk about TV.

Do you know how hard that was when there was a strike at the start of the last season?! Supporting SAG and the WGA meant not promoting shows, so we happily pivoted to the details of the strike, independent media, reality TV, documentaries and animated shows that weren’t on strike (make sure you support TAG in their current negotiations, though!) But really, all I wanted was to talk about things that weren’t TV.

So, I’m starting Deep Trouble. A place for me to write deep dives into topics and other events that interest me. If you’ve been a fan of the pod or newsletter, you already know I love to do this! The JonBenét piece probably didn’t come as a surprise to you.

If you’re new here, Deep Trouble will be more stuff like this:

Read

• The Dueling Docs Series - On Wisecrack this week, I mentioned that the best way to understand how a documentary might be manipulating you is to watch as many as you can! In this long-running series, I watch multiple docs on the same topic and compare them for you.

• The Murder of Laci Peterson vs. American Murder - This is one of the best examples of a documentary creating a manipulative narrative and it’s a favorite in the Dueling Docs series. I almost thought Scott Peterson was innocent until I interviewed Beth Karas and she walked me through the case!

• The Problem with Below Deck and the Case for Reality TV Unionization - Oh, I will still be talking about reality TV. Don’t worry about that.

• Documentary Recommendations! - Did you miss the old ones?

  • 2022

  • 2023

  • 2024

• Weird Personal Stuff!

  • Why do I own a Skin Fridge?

  • What happened when I tried to go on 52 first dates in a year (these posts will be migrating over to Deep Trouble!)

  • Why Dov Charney Owes Me Money!

  • Racism

• My Hot Culture Takes

  • I saw Slave Play twice just so I could tell you what’s wrong with it!

  • Why I think we’re entering a new era of cults

  • Yes, I’m Polyamorous (someone on Twitter thought it was a bit)

Listen

• Podcast episodes similar to these, but not just about TV:

  • The Curious Case of Natalia Grace - I sat down with CourtTV reporter Beth Karas to talk about The Curious Case of Natalia Grace! The lies, the truth and everything she learned working on the documentary released last year. We talk about the second season here.

  • Seth Rogen and Roxane Gay on 90 Day Fiancé - Like I said, I will never stop talking about reality TV.

  • Jason Mantzoukas - I am still willing to talk to him about whatever he wants.

  • The Truth of the Golden Bachelor with Laci Mosley! - I had to talk with the Scam Goddess herself when I found out the first Golden Bachelor was a dog.

  • The Grey’s Anatomy Scammer - Anatomy of Lies on Peacock is a great documentary about the woman who scammed her way into the Grey’s writers room and this looks at her impact on the narrative.

  • Seeking Sister Wife and What’s Really Real on Reality TV - Does that guy with three wives really looking for a fourth? Well, I am always happy to figure out what’s TV and what’s real.

If that sounds good to you, welcome to Deep Trouble! If not, well, I understand. I will still be talking about TV and doing reviews by request over on Patreon! That’ll be TV I Say now. You’ll get two review posts and a podcast episode about everything I’m watching and like every month. If you only want TV takes, there’s still a place for you.

In 2025, Deep Trouble is bringing you more long-form written pieces, podcast episodes, hot takes and funny culture pieces. I hope you’ll stick around!

-Ashley

p.s. if you didn’t pick up on it, deep trouble will be A LOT of links, footnotes and internet tidbits too :)