You certainly can pop a wheelie on a cruiser; I've seen a guy on a VTX 1800 do it. It all depends on a lot of factors (like weight of the rider, tire grip and conditions, mechanical condition of the bike and it's set-up, how quick you pop the clutch and hammer the throttle, etc., etc.). A v-star 1100 has a fairly low weight, and if he has modified it at all (like with the Max Air predator kit and re-jetted it) or not and if he isn't a very big guy it definitely could get some air under the front tire.
Cruisers aren't really supposed to be doing them, but it can be done. With the sheer weight of them, you're asking for trouble if you start trying to do it.
By the way, if you run with any guys trying to do a "stoppie" on a cruiser...stop riding with them because they're just plain stupid.