First - congrats to bk (and Mark & Craig) for their perseverence in keeping HHW going (and going and going.....). The only thing better than chatting with the gang is meeting them in person (Jason, Jose, Juiliana, Susan and all - what a lovely bunch of coconuts we are!)
Taking the lead from a fellow HHW'er, here are my top 3 in each group:
Vintage male - Sammy Davis Jr. (what couldn't he do?), Frank Sinatra, Mel Torme (fog indeed)
Vintage female - Rosemary Clooney, Ella Fitzgerald
Modern male - Michael Bublé (only one album, but what an album!), Michael Feinstein
Modern female - Diana Krall, Nancy LaMott (RIP), Jane Monheit (a work in progress)