Over the holiday break, despite being sick, we were able to squeeze in a few sessions of high level play using character that haven't seen action in many years. This is mostly because they have few adventuring peers and play tends to focus more on low or mid-level characters coming up through the ranks. Still, it is nice to break out the old leviathans from time to time.
My eldest son, 14, was able to take over the GMing reins so that I could play Lord Grimslade Flamewalker, a 16th level elf. I made Grimslade on 2.8.87 and he is the most successful character I have ever developed. When I first made him he was a member of an adventuring party, and the weakest one at that. He had either -3 or -5 combat adds to start with. Strangely, the rest of his party all died within an adventure or two, despite being "superior" to him in every way. Yet Grimslade, who in his early days went by Airwalker after obtaining the eponymous cloak from the Treasure Vault* in an early game, survived many adventurers through the years (even though I GM 90+% of the time). At this point he rarely does more than put on cameo appearances, but we thought an actual adventure would be the way to go.
My wife played Grimslade's wife - Starlight, a 14th level human wizard, a family friend played Zoey the hobb(it) rogue, and my third oldest son (10) played Captain Firebeard, a 7th level dwarven warrior with powers vastly beyond his level due to a trip through Jason Mill's awesome adventure, Something in the Wind (see The Vital Spot website). For the second session, my second oldest son joined us with a 9th level imp rogue created from Michael Eidson's freshly revived 5.5e character generator at the Troll Mystic website (having no suitable PCs of the desired power of his own).
I will have to ask my son to post a brief synopsis of the setting and adventure here, as it is far richer than I can convey. It was an adventure/dungeon he created to provide what he thought would be a suitable challenge for us. The delvers traveled to another world of extremes to defeat ice trolls and isocroms (magic eating monsters) in a mountain fortress. The isocroms forced us to abandon all spells and magical items save for those of the highest levels. I was a little concerned because I didn't know how well high level T&T play would hold up, not having done so in almost a decade - we were facing monsters with 5,000 MRs on this adventure, after all, with 20th level saving rolls being nothing special. I have to say that the sessions went very well and T&T can handle high level, creative play no problem. Yes, the MRs and SRs were through the roof, but they are scalable for a reason, and they worked well.
We have probably one more session to finish off this adventure. We've already decided that at least a handful of times a year the Great Old Ones will get to come out to play.
*A Catalyst product by Flying Buffalo. It was a staple in my early games, along with all of the other great Catalyst products like the CityBooks, Grimtooth's Traps, Lejentia, Wilderness Encounters, et al.