This is a retrospective study of 63 patients presenting with stage four laryngeal and/or hypopharyngeal squamous cell carcinoma. The aim was to define the factors influencing the oncological and functional outcomes of the patients. All patients had T4 lesions with extralaryngeal extensions and were not suitable for organ preservation protocols. All underwent total laryngectomy with or without post-operative adjuvant therapy. The following factors were studied: age, sex, comorbidity, site and stage of the lesion, post-operative treatments, recurrences, causes of death, quality of feeding and phonation. The main factors affecting the oncological outcomes were: female sex, ASA >3 and vascular tumour emboli for OS; female sex, tumour emboli and hypopharyngeal site for DSS; female sex, tumour emboli and extracapsular spread for recurrence free survival (RFS). As regards functional prognostic factors, the only negative factor for deglutition was a circular pharyngectomy and for phonation the N stage. This study confirms the reliability and efficacy of upfront total laryngectomy in patients with advanced laryngeal and hypopharyngeal carcinoma.