No shit sherlock. I dare say with the right technique and practice you could perfect it, perhaps using some wee tool to breach the skin after which with enough momentum you would get through no bother, much like after a balloon is popped. Who knows but he also risked a kicking each time he did it no doubt.
Plenty of wee tools on orange walks, right enough.
Getting back to the cartoon possibilities of your imaginative story though. I could just see him making it through the the first side of the drum but not the second. Being stuck inside the drum would over balance the drum carrier, causing him, the drum and the stuck acrobat to take off, at a fair rate of knots, rolling down the hill, being rapidly pursued by the rest of the band who had now broken into Benny Hill style chase music.