As so often in matters where Nature is involved, it all depends.
What species of deer; what rifle and cartridge; what weight and type of bullet; where are the deer and how easily can you find one if it is only wounded; are you absolutely sure that the one behind is a genuine cull animal and not just a chance to show off your shooting skills; can you, your family or your dealer cope with both animals at once; can you get them to clean storage facilities quickly without making two trips?
And those are just a few of the things to consider before trying what is, in reality, a trick shot.
Such shots are occasionally taken and sometimes under perfectly reasonable circumstances but I would personally be very reluctant to try it other than in a park where, if a deer is wounded, it can be followed up and dealt with quickly.
Bullets don?t always travel in a straight line after they hit a deer and that is particularly so in the case of small, high velocity bullets.
But with any bullet, if you hit bone, all bets are off.
I remember many years ago shooting a Fallow pricket at a range of about 40 yards.
The deer was broadside on and the bullet hit the spinal column at the base of the neck, killing it instantly.
The bullet then altered course 90 degrees and exited beside the anus.
The rifle was a 7×57 and the bullet a 140 grain Nosler Partition.
I wasn?t trying to kill two animals at once ? and I never have tried to ? but you get the picture, I?m sure.