Diabetic striatopathy (DS), also known as non-ketotic hyperglycemic hemichorea, is a rare condition that arises from uncontrolled hyperglycemia. It is characterized by new onset movement disorders, changes in the striatum on imaging, or both. DS can occur as a complication of long-standing non-ketogenic hyperglycemia or be the first presentation of previously undiagnosed diabetes mellitus (DM). Additionally, uncontrolled or rapidly corrected hyperglycemia can, in rare cases, lead to osmotic demyelination syndrome (ODS). Although ODS typically occurs after the rapid correction of hyponatremia, the same effects and symptoms can manifest in patients with diabetes when hyperglycemia is corrected too quickly. We present a 59-year-old male with a history of uncontrolled diabetes mellitus and cerebrovascular accident who was brought to the emergency department by EMS with a new onset movement disorder. This case demonstrates a rare example of a patient presenting with classic imaging findings of both DS and ODS. Specifically, the patient demonstrated unilateral basal ganglia hyperdensity on CT, indicative of DS, alongside central pontine diffusion restriction and T2/FLAIR hyperintensity, consistent with ODS. This report discusses a rare case of the simultaneous occurrence of diabetic striatopathy and osmotic demyelination syndrome in a patient with uncontrolled diabetes mellitus, highlighting the intricate neurological complications of hyperglycemia. These findings stress the importance of timely recognition and management of hyperglycemia-related conditions, with imaging playing a pivotal role in diagnosis.