Hmmm..

Lollipop
A Milli
Fireman
Got Money
Shooter
Fireman
Hustler Muzik
Money on My Mind
Weezy's Ambitions
Swag Surf
Ice Cream
Put Some Keys On That
Upgrade U
Go DJ
6 Foot 7 Foot
I'm Single
Right Above It
Cannon
I'm Me
I Feel Like Dying

Kanye can as well if you count his production discography but these usually only work if you put the artists against people from their own generation. Wayne & Kanye got the nostalgia edge for them

Putting my Drake d***riding aside Kanye might but I give Wayne a better shot bc of the magnitude of the hits
Lollipop is revolutionary

Drake and Rihanna hit battle would be fun

disturbia
work
we found love
birthday cake
b**** better have my money
umbrella
diamonds
man down
only girl
pour it up
pon de replay
rude boy
sos
stay
this is what you came for
unfaithful
whats my name
where have you been

jheeeze

Drake and Rihanna

Wayne and Kanye make more sense to me.

I would like to see jay z vs drake

There’s actually a Drake v Rihanna battle happening this Sunday and a lot of ppl on Twitter are hyped for it

Unrelated but they need to stop having one person go first every time. Getting to respond to what the first person played is a huge advantage

I’m kinda surprised Drake hasn’t issued an open challenge to battle him. Seems to be a competitive guy and has said before he wished rap was more like sports with wins and rings. Well here’s your chance