I would totally take Everybody over Like A Virgin and Material Girl.
Everybody is iconic. Just hearing "let the DJ shake you" echoing across the arena during the intro would send everyone into a frenzy.
No don’t worry I love Bitch I’m Madonna and disdain Girl Gone Wild. Everything is fine and in cosmological order.
Asking for weak deep cuts off flop albums from a poor decade artistically on a celebratory Greatest hits tour... pls. It's giving 'Spirit...
I usually play it back to back with:
Separate names with a comma.