Preoperative radiological findings of hypopharyngeal cancers are used to determine suitability for surgical resection. We sought to examine preoperative imaging characteristics to determine how well imaging findings predicted surgical resectability. A retrospective case-control study of patients undergoing a pharyngolaryngectomy in a tertiary referral center over a 2-year period was completed. Demographic details, previous treatment, subsite, TNM staging, imaging characteristics, and operative characteristics were collected. A total of 78 patients met initial inclusion criteria, of which 71 patients ultimately underwent successful surgical resection (91.1%). Preoperative images identified suspicion of prevertebral fascia invasion in 24 (30.7%) cases and carotid artery involvement in 14 (17.9%) cases. In cases of suspicion of prevertebral fascia invasion (24), 19 cases (79.2%) were resectable, and in those with carotid artery involvement (14), 11 (78.6%) were resectable. Concern for prevertebral fascia invasion on radiology led to a higher likelihood of a close margin (42% vs. 17%) in those without concerning features (p = 0.088). The present study demonstrated a high rate of resectability of hypopharyngeal and upper esophageal cancers despite imaging findings suspicious for factors that could limit resectability. In patients with advanced hypopharyngeal, especially in the salvage setting, surgery should be considered.