Pittman was born in the small town of Talahina and raised in Cleveland County, Oklahoma. At eight years old he began taking piano lessons under the encouragement of his mother,but later began sneaking into his older brother’s room to play on his drum kit. By age fourteen,he had switched to guitar and was soon introduced to the mysterious sounds of Lightnin’ Hopkins and Muddy Waters by Bracken Hale , a good friend and member of his seventh grade football team. Their friendship would prove significant as Hale would later collaborate with Shawn on writing material for many of his albums. He was also turned on to Elmore James and Albert King by Tulsa native and early guitar mentor Bernard Bigby.