I like to crowd-source playlists on social media. I drop the theme, and the hive mind does the rest. The results are always amazing! We play them at the Nearly Monthly Geek Radio Daily Poker Night
Quintessentially Them - we all have favorite artists. What's that ONE song of theirs that you would recommend to get started
The Color of Music - songs with colors in the titles. Is Raspberry Beret cheating?
On My Way Home - songs with some variation of home in the title
The Aughties - favorites from 2000-2010
Pick Me Up - songs that are guaranteed to raise your spirits or pump you up
Covers - all the songs you love, from a slightly different point of view
Poker Night All Requests - An hour and a half of fun
Essential 90's - the songs that take you back
Quintessential 80's - these take you WAY back
Personal Top 5 - any genres, any artist, any way you want it
Karaoke Favorites - songs you love to sing every time you hear them
Poker Songs - a bunch of songs that have a gambling theme. Warning, it's a somber list at times!