Most of my experience in the Drake Hotel has been in the underground. They have an excellent concert space in the basement which is pretty much in constant use by local bands. Occasionally something a little more outside the box will occur, like a cabaret, or a cabaret for the dead.
Every Monday, the Drake is host to Elvis Monday's, a long standing event that's been happening in Toronto for a really long time (like 15 years I think?) It's been hosted in several venues over the years, but lately it called The Drake home. Elvis Mondays, in addition to offering free local music, offers free food! There's usually a delicious stew or something equally wholesome available to everyone.
Drinks here are a bit pricey, in the 6-7 dollar range for a beer, and about the same for a mixed drink I think.