Indigo Flower of the ValleyEdit
Once a hobbit, after being corrupted by the One Ring, took the Ring deep into the tunnels of the Misty Mountains.
Game of RiddlesEdit
He encountered Bilbo Baggins who found his ring lying on the floor after struggling with a Goblin. They decided to have a bet: If Bilbo won the game of riddles, Gollum would show Bilbo the way out. If Bilbo lost, than Gollum would kill and eat Bilbo whole. Bilbo eventually won, but Gollum betrayed Bilbo and instead chased Baggins. He lost Bilbo when the hobbit discovered the ring was magical. Bilbo almost killed Smeagol but then, he saw another side to him, pitying him and then said he'd hate Bilbo forever.
War of the RingEdit
Later, Gollum chased Bilbo Baggins' and Violet Greenhill's son, Frodo Baggins and their granddaughter, Hazel Bolger, and the two fo them agreed that Gollum would come only if he didn't attack them.