This is a really good question. I like to bake some quick forms of play into stuff we're already doing, like all-team meeting and virtual retreats. The more lightweight this is, the better. I think the reason some things fail is that they're too complicated. Nobody wants to play an online game that has super complicated mechanics and takes 2 hours to learn, when you only have 30 mins to play. Simply taking turns sharing your screen and playing Quick, Draw! or playing around on a silly Miro board for a few minutes gives me way more mileage.
Something else rolling around in my head related to social / fun things at work:
Personally, I kind of hate when games and icebreakers are set up as separate, mandatory or mandatory-ish things that people are expected to attend and laugh uproariously at. I come to work to work, and it's extra nice if I also enjoy my colleagues' company and we have fun together in the course of that work, but I've got plenty of friends and fun outside of work and I don't need work to facilitate that for me. Why is "engagement" thought of as a primary measure for how good of an employee someone is? It's possible that they want to give 100% to their work, and have 0% interest in the social side. I think that should be normalized and okay in the new remote future we're creating. When we look at "disengaged" employees as problem children because they don't show up to every clam bake super enthusiastic, that feels like another office culture problem we're dragging into the remote culture space. And rewarding extroverts, big-talkers, and party-lovers over people with equally good though different characteristics. Let's not! 🤷🏻♀️