Trainwreck Share definition Flag An obvious Trannie, or transexual, someone who was born one gender, but later in life changed to the other. Hey, dude! Did you see Matt making out with that trainwreck?! Trainwreck by whattup August 7, 2008 0 0 Get merch Get the Trainwreck mug. Buy Now — $32.95 See more merch