Spinal Tap.
With Leon Redbone playing the late-night after party when the big crowd has left.
Very cool choice.
I’m pretty sure it would take the whole lot, but I would try for Kate Bush. Failing that, I’d hire a whole bunch of talented women to play a Kate Bush tribute festival, mixing their own stuff and their favorite Kate songs - Happy Rhodes, Tori Amos, etc.
If i had a sudden influx of Great Amounts Of Cash… i wouldn’t contract an expensive Musical Act, i’d hire an Investment Counselor /accountant.
Won’t go far if it’s all being Spent…
Asleep At The Wheel, or Dropkick Murphys.
Elvis Presley. How much would it cost to bring him out of retirement?
U2. Only if they do pre-Pop music.
Ha ha. Well if that’s how we’re going to play this game, then I’d bring Bobby Darin out of “retirement.”
Not if you drag that delusional hussy into it, no. 
I’m like that Carnegie Hall lady (Wiki says Florence Foster Jenkins). The only thing I would want is for me to be the one on stage singing in front of a big audience. I wouldn’t mind having Stephen Colbert come out for a duet, though.
ZZ Top. They don’t even live that far away and some of their old friends will be there too.
Alice Cooper
Rush
(Hey, as long as I’m fantasizing, I choose to fantasize that I won a big enough pot that I can have two parties! Though a double bill with Alice and Rush would be fun. :))
Genesis. Peter Gabriel would also have to sing a few too. I choose the songs.
Porcupine Tree would open up.
You know, I’ve seen this mentioned before and thought you were kidding. Wow!
I don’t get your reply. I’m sure most entertainers have a price they’d come out of retirement for.
Ahhh, you had me going there for a moment…
nm
She is. Kidding, that is.
I would hire The Waybacks, MonkeyJunk and Paul Simon.
Oh yes!
Daft Punk
Madonna. 10 a.m. at a Sunday brunch on the vast patio of my 100 acre estate.
Hahahahahahahahahahahahaaaaa! Just kidding! Madge would be all wrong in the daytime. Harry Connick Jr. or Michael Buble would be my choices, I love both.
If it was a wedding, graduation, funeral - something with some formal ceremony - I would rent use of a stunning castle in Scotland or Ireland, and hire the best bagpipers. The Black Watch, perhaps. (Maybe the Dropkick Murphys at an evening party.)