Large vallecular masses are an uncommon disease entity which includes a wide spectrum of rare pathologies. These masses may present as purely vallecular in location or appear as an extension from adjacent anatomical sites like tongue base including lingual tonsils, epiglottis, palatine tonsils, epiglottis, and the remainder of supraglottis. Literature review reveals very rare conditions presenting as vallecular mass lesions. The imaging features are generally diagnostic for characterization. However, these masses can exhibit indeterminate appearance at imaging. We present a series of five cases which includes two rare presentations: a case of low-grade cribriform adenocarcinoma of the base of tongue and a vallecular lipoma. The other three cases presented for differential diagnosis including benign vallecular cysts and two cases to show that malignant masses arising from neighboring anatomical sites such as tongue base or supraglottic larynx can exhibit significant vallecular component.