Aortic dissection (AD) is a serious condition in which the intimal layer of aorta tears and blood surges in between the intimal and medial layers of aorta causing it to separate (dissect). It usually presents with excruciating pain radiating to the back. Here we present a unique presentation of AD where an old-aged Caucasian male presented with a chronic history of intractable hiccups. His computed tomography (CAT scan) revealed the dissection of the descending thoracic aorta. He was managed conservatively and was discharged home in stable condition. The purpose of this report is to highlight this unusual presentation of AD and unmask the possible etiology of hiccups in such cases.