I was an Orc Barbarian i believe (this was 6 years ago, you’ll have to forgive me). We had just escaped a near death opening sequence involving dozens of goblins inside a cave and traveled to a nearby metropolitan area. We had a bard on our team who had chosen to travel a different route than i had. I strolled down a popular street and noticed a very nice, almost posh, music store.
I was broke, because as i said we had just left a very jarring opening sequence, but regardless noticed two particular items that i wanted for myself and our bard. I decided to attempt to steal the items (a bad ass guitar and a solid gold lute). The rest of the party thought i was insane, and the DM even gave me the option to reconsider stating that everybody who has ever tried stealing from this store was killed. I tried it anyway. I had no clothing on to hide these items, so that makes this a little funnier.
Dm tells me to roll D20 for distraction. Nat 20, i literally pointed at a wall, took the items, and walked away. I was the first successful theif to ever attempt to rob that store, and the DM was crushed. I gave the lute to our Bard who later purposely threw it from a Zeppelin to prove a point.