Back in my teenaged days, a 3" 12 gauge shell on a dragonfly, plus a few box turtles with a 35 Remington Marlin.
Scored a double on a couple yotes at a little over 200 yds with my 338 Ultramag while elk hunting once. Middle of the day, hot, no elk. I do believe I got some expansion of the 225 gr Accubonds judging from the exit wounds, yuck!