A film that I've always been a little bit partial to is 1995's A Goofy Movie. While it's not the best movie ever made, it's definitely not the worst either! There's a lot of overdramatic angst for a movie about Goofy, but I can't help but enjoy it EVERY time I watch. I think the songs in this film are some of the catchiest show tunes that have ever come from a Disney movie! Not only that, but there's something I like about the concept of a father-son road trip being a made into a musical. Comforting is probably how I'd best describe it. Despite its many uncomfortable moments (that Max is a real jerk!) I get a nice sense of comfort watching it.
So... yeah. There you go. My two-cents worth on A Goofy Movie. You're welcome, internet!