The series of shorts focus on two or more characters talking about their respective lives or the world around them.
The series was originally pitched by Lachie to have a slightly darker tone compared to the main series (being PG-13) but Milan decided to make it more family friendly.
Holiday Shopping is the first episode of the Crotoonian Conversations series. It was originally uploaded January 2nd, 2016.
- Lachie Vincent storyboarded this short and let Milan choose which engine Mr Grumpy would say goodbye to. He ended up chosing Cardean to give the character some publicity.
- The short itself was originally going to be a 'cold opening' for the Christmas Vacation music video, until it was decided it would be better suited as its own individual video.
Loads of the Day
Loads of the Day is the second episode of the Crotoonian Conversations series. It was originally uploaded on April, 21st 2016.
Spooks at Sea!
Spooks at Sea is the third episode in this series. It was originally uploaded on October 20th, 2017.
- Skipper Stu
- Jack Skellington
- Frank and Eddie
- Diesel (cameo)
- Duck (cameo)
- Victor (mentioned)
- Salty (mentioned)
- The episode was originally recorded and worked on for a 2016 release, but was pushed back due to scheduling issues. It was completed within 3 days in 2017, and was finally released that year.
Loco in the Poconos
Loco in the Poconos is the fourth episode in this series. It was originally planned to air as part of Crotoonia's On the Road, but was ultimately released separately on July 6th, 2018.
- Strong Bad
- Sir Topham Hatt (does not speak)
- Mr. Grumpy
- Sir Allen Featherington
- Homestar is holding a box of cheese curls branded "Cheesel T Poofs". This is a reference to the character Cheesel T. Weezel from the movie "Foodfight". It's tagline "A perfectly good bag of America's Favourite Off-Brand Baked Cheese Snacks!" is a reference to the film's infamous quote "That was a perfectly good bag of chips!" (notorious for its cheesy and overdramatic nature).
- Mr Grumpy and Homestar's "camping trip" sequence is a direct reference from a cartoon from Homestarrunner.com, specifically Strong Bad Email #182 Business Trip.
- The song on the radio was originally going to be "Lay All Your Love on Me" from the "Mamma Mia" soundtrack (an in-joke between the crew) but was changed to avoid copyright problems.
- This short contains the first instance of mild language, via Strong Bad.
Incidental Perfection is an eight minute Christmas special of this series which was meant to air on Christmas 2017, but later premiered in Christmas 2018.
- Donald and Douglas
- Strong Bad (does not speak)
- The Cheat (does not speak)
- Strong Mad (does not speak)
- Strong Sad (does not speak)
- Gordon (cameo)
- Percy (cameo)
- Rosie (cameo)
- Peter Sam (cameo)
- Mighty Mac (cameo)
- Victor (cameo)
- Casey Jr (cameo)
- Calley (cameo)
- Olwin (cameo)
- The first few minutes of audio from this episode was showcased in the MilanToon the Halls livestream.
Spoiler Alert! is the fifth episode in this series. It premiered on May 5, 2019.
- Strong Bad
- Homestar Runner
- The Fat Controller (does not speak)
- Tillie (cameo)
- Big Tim (cameo)
- Whiff (cameo)
- Johnny (cameo)
- The first episode to be co-animated by Lachie Vincent.
- The Action Chugger film Golden Window is a spoof of the third James Bond film, Gold Finger.
- T.J. summarises the ending to the 1997 sports comedy Space Jam.