On a LEOG recorded after the third Spill Dot Con, when Leon told this story (this is paraphrased, mind you):
I took a couple of Spill members to see Midnight in Paris. When we walked out, I asked them 'Wouldn't it be awesome to hang out with all your heroes like that?' and they said 'Well, that's happening right now'.
YMMV on whether its Heartwarming or Dude, Not Funny!, but after it was revealed that Randy was diagnosed with cancer, he and the rest of the LEOG crew just keep cracking jokes and didn't let it bring the show down. Despite the fact the jokes cross the line twice, even the ones Randy makes, you really get a since the closeness of the crew and how much they care about Randy.
Gets into Tear Jerker territory when they reach the final musical transition before Leon and Cyrus wrap up the show. It turns out to be a compilation of just about every one of the main cast members giving individual eulogies to the show (and the fans) with Sia's "Breate Me" spliced into the background. The song itself is a direct Shout-Out to the series finale of Six Feet Under (something that Grant is quick to point out).
May be a bit different than the rest listed here, but Jeff and Jason have grown so attached to their horse Greedo in their Red Dead Redemption playthrough (eventually stating that he's as much as a Memetic Badass as JohnMarston), that they always make sure to avoid accidentally killing him during missions. If they do (or, more accurately, Jason does), then they make sure to reload the game to a point before he died.