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  • Last Year's News Today: Forming Links with Pineapple


    26 Mar 2025 Jess Williamson Content Co-Director
    18 min read Unlisted

    The Origins of Pineapple News

    Jess PFP

    Hello and welcome to a new segment we're doing. We just came up with this about two days ago and we have no idea what to call it. Today we're talking with Pineapple of Pineapple News. Hello.

    Hello.

    Pineapple PFP
    Jess PFP

    So this month, if things go to plan the finale of Pineapple News should be close to release, but I wanna take this time here today to sort of ask some questions.

    Okey dokey.

    Pineapple PFP
    Jess PFP

    (laughs) I know that Pineapple News, in some form, existed before Wii Room, so I was kind of curious to ask, what is the "origins", if you will, of Pineapple News.

    So originally I wanted to start doing more skit content, if you will, on my YouTube channel. And so I thought, "Why not poke fun at news channels that cover video game news". And so I just did my own spin on that. And it was supposed to be a one time thing. But people liked it so I was like "You know what why not keep doing it?". I had fun doing it, especially compared to the stuff I used to make, I felt like I could be more free with my comedy and my storytelling enough that I thought we have a really good thing going here, why not make this a short series. And now we're here, with (when this will come out) at least 7 episodes are out. (There isn't)

    Pineapple PFP
    Jess PFP

    Yeah. I have no idea if this will be before or after the finale. Even talking about it now the finale isn't done yet, I don't think we'll be talking too much about it today.

    Assembling a Crew

    Jess PFP

    This is the first time in any WiiLink Original that we have actual other people in real life. It's crazy.

    It's rather insane.

    Pineapple PFP
    Jess PFP

    I want to ask, how did it start, how did they become involved, all that stuff.

    Out of the cast if you will?

    Pineapple PFP
    Jess PFP

    (laughs)

    So originally it was supposed to be just me and there would be a character, but it was basically like schizophrenia, you would never see them but I would just "respond", and that was most of the first episode. And then for the second episode I was like "if I'm gonna do a sequel I might as well have someone else actually be there." So we have the introduction of camera guy in episode 2, who we later know is named Dean, and he's got an attitude, I wanted to add a character who would be like a reality check, obviously the setting is more comedic, and a lot of the things I say and do in the show would be things I would never get away with in real life. I would probably be fired on the spot. So Dean is the reality check where he can say "you know you should not be doing that" or just starts fights. Then we have the manager whose name is Manager. The reason why he's called that is originally I just could not come up with a good name, I'm terrible with giving characters names. So I thought for the joke what if the manager was just called; Manager. Manager kind of plays the same role as the camera guy in that he is sort of a reality check, takes things more seriously and just makes sure he can keep his job. And later in episode 7 we have Peter, and he is kind of the opposite of our main character. He's a lot nicer, actually cares about other people. Not egotistical. And these are all my friends. I've done a lot of projects where they've played roles before so this wasn’t anything new.

    Pineapple PFP
    Jess PFP

    It very much was a continuation of the projects you’ve done for quite a while at this point.

    Yeah. And originally I wanted them to play the same character, but it just didn't work. So in the end these are all different characters from other projects.

    Pineapple PFP
    Jess PFP

    So originally they were supposed to be the same characters in the same universe.

    Yeah so originally it was supposed to be the same cast and it would be another sketch involving Pineapple (character) makes a news show so he hires his friends. But then I was like “that’s stupid”, so I scrapped that idea. So it’s a brand new story, these guys are not “friends”, and you can tell from most episodes they do not have friendly conversations, they’re mostly arguing and fighting.

    Pineapple PFP
    Jess PFP

    Almost like a “Pineapple Reboot” if you will.

    Basically yeah. It’s like if I was making a new show but I didn’t have the budget to hire new actors so I just reused them.

    Pineapple PFP
    Jess PFP

    Just like Wes Anderson.

    Just like Wes Anderson.

    Pineapple PFP

    Sketches within Sketches

    Jess PFP

    There’s “breaks” found in the episodes, as of recording we’ve seen three of them, and while episode 1 and 2 had very short segments, there’s a break segment in episode 3 that almost takes up half the episode. I was curious how that came to be, considering that it had a very improvised feel compared to the other ones.

    Originally when I made the first episode it was supposed to be a joke on how news channels will say “we’ll be right back after the break”, and it was inspired by that. So the original gag in episode 1 was that they literally had no money for commercials, they had zero and they couldn’t promote anything. So all they could do was just, smash an egg, and that was it. And even in that episode the character alludes to say is that all they can do. So it went from there so I went y‘know what, this could be a segment where I can do skit ideas, and can compress that into a commercial.

    Pineapple PFP
    Jess PFP

    Mhm.

    So episode 2 is just Quagsire telling A.I. jokes. But episode 3 which was the chef skit, it became moreso about mini-ideas that I wasn’t confident in it as a full length sketch, but I could compress it into a Pineapple News episode. And I think it works better that way, but I don’t know how people took to that. It’s just now a thing where even if it’s a short thing it’s important to the episode. In my opinion it’s what makes Pineapple News, Pineapple News.

    Pineapple PFP
    Jess PFP

    It’s become a vehicle for smaller sketches.

    Basically.

    Pineapple PFP
    Jess PFP

    It makes sense, as of now Wii Room Reels does not exist so we can’t make short form videos and ruin people’s attention.

    Unfortunately.

    Pineapple PFP

    A Holiday Rush

    Jess PFP

    I remember when we were producing what was unofficially season 1A, we barely managed to get the holiday special out on time. I was baffled by it even making that deadline, but I want you to sort of share your experience making that episode because I remember some horror stories from January.

    So in the background, even from filming to editing it was not the greatest experience. I was super ambitious, I wanted the episode to be very special, a lot of that having to do with it being on Wii Room and it being a “holiday special” and to have people look forward to it. So I wanted people to think it was really good. I didn’t have all the time in the world to make this either, I did have a time limit. So I did end up having to push some people around for it to happen, but the hardest part was the editing. You can testify to this.

    Pineapple PFP
    Jess PFP

    Yeah I remember.

    There was a point where I did not sleep at all trying to work on this, and then having to actually upload it to Wii Room was a whole other nightmare. I was uploading this at the highest quality which meant it took forever, and when I did upload it there was an unfinished part. So I had to spend another 20 minutes to get that done, and then it was uploaded essentially at the end of the day. With all the stuff that went wrong with filming and editing, I’m still happy it was done relatively on time. It was definitely one of the biggest projects I had ever done. There’s two original scores, I commissioned special art for it, it had a lot of characters. And this was one of the longest live action stuff I’ve ever done too. It was a challenge, but I’m happy with the way it turned out.

    Pineapple PFP
    Jess PFP

    There were several cameos you had to organize too.

    Oh yeah I completely forgot about that. I wanted to have cameos to make it feel special.

    Pineapple PFP
    Jess PFP

    Speaking from personal experience I’m not very proud of how my cameo looked. (laughs) But if I remember correctly you asked for cameos in our developer Discord server. I believe there were 2 on that initial proposal, but there were 3 in the actual episode. Did you personally ask someone for it, how did it go?

    There were 3 cameos from the team. There was you (Jess), there was Kolton (KGR), and then there was Isla (at the time known as Harry) who was the voice of Jeff the Comedian. She didn’t have a visible appearance, you and Kolton did, but she did play a character, just as a voice role. Those are really the only three that I asked for.

    Pineapple PFP
    Jess PFP

    How long was the episode again? I remember all of the appearances were pretty spread out.

    I think it was 16 and a half minutes. It was very long.

    Pineapple PFP
    Jess PFP

    I think it’s fair to say you can be very proud of what you made. I thought it was very good. It also makes a lot of sense why that episode was the last episode for about 2 months.

    It is funny because season 1A ended up becoming about going from nothing and in the end becoming something, and now with episode 5 and beyond it’s sort of become popular. Maybe you could consider these 4 episodes season 2.

    Pineapple PFP

    A Creative Remaster

    Jess PFP

    You said Pineapple News was originally a series of sketches on YouTube. This show poses quite a unique challenge where you had to work around episodes you’ve already made. How did that work? I assume a lot of the current viewers hadn’t originally seen the episodes on YouTube, so a lot of them probably don’t know what was changed or added from those original cuts.

    The biggest changes were those opening scenes in specific episodes in black and white. It’s a completely new subplot showing me in present time thinking about how Pineapple News didn’t last long. All these episodes start with a date from 2023, 2024, and obviously we’re not in those years. So we know it didn’t last long, but we don’t know why. So the scenes hint at the turmoil the main character is facing and that’s going to be a big part of the series finale. Another thing is just the credits sequence. I made it more fun.

    Pineapple PFP
    Jess PFP

    (laughs)

    I added better music, each one ends with a backdrop from the episode now. It isn’t as major but I also retooled some things, like adding sound effects or just cutting everything just a little better, so it’s just mostly a better version of those episodes.

    Pineapple PFP
    Jess PFP

    So it’s almost like a remaster. Can we call it “Pineapple News Remastered”?

    Remastered Plus.

    Pineapple PFP
    Jess PFP

    I remember when we released the first episode in December last year, which by the way, that episode has like 2000 views at this point.

    I know, I check once in a while and it’s gone up like crazy. People are still watching it.

    Pineapple PFP
    Jess PFP

    Right. So when we released that I remember the response at the time had some confusion about how the episode took place in 2023. Was any of the additions since episode 2 affected by that response?

    These episodes were originally released on YouTube the day the news actually happened. So the first episode was on November 2023, and the episode itself was actually from November 2023, so on and so forth. So now that it’s not released like that anymore, I added the date in the beginning to let people know about it. Originally that was my method to tell people, since that’s the first thing on-screen, not counting the WiiLink Originals intro. I’m pretty sure I’ve read most of the opinions said about the pilot on the WiiLink Discord, and I don’t blame them for being confused. A lot of news shows talk about things happening right now, like Homebrew Tea. So having a news show take place at late 2023 is very confusing and I don’t blame them.

    Pineapple PFP
    Jess PFP

    There’s a huge gap in the market for news from 20 years ago.

    Yeah that’s true, who wouldn’t want to listen to that? Probably better than the stuff going on now.

    Pineapple PFP

    A Peek of Season 1B

    Jess PFP

    I want to close by asking you, as of recording (March 5th), we haven’t seen anything about season 1B. And even when the episodes are out at this point, there’s probably a lot of people who only follows our news posts here and haven’t seen those episodes yet, or haven’t realized the show’s back. Do you wanna tease them about what’s coming in season 1B?

    There’s a couple new characters, a couple new environments that you’ll see Pineapple in, there might even be a story about getting over grief. There’s a lot more stuff in these episodes that I think are just season 1A but better, I do think these episodes are a lot more high quality, a lot more story driven than just the news, there’s a lot more character interactions. I can’t wait for what people will think about the new characters and interactions, and what crazy low budget special event I can do after the cooking one. Be excited.

    Pineapple PFP


    Watch Pineapple News every Sunday, or watch the first 5 episodes right now, streaming exclusively on Wii Room.

    Featuring:

    Pineapple - The Pineapple Gaming Show on YouTube, @themrpineapple on Twitter

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    Jess Williamson
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