This case report details a rare case of Grover's disease in an 80-year-old Caucasian male complaining of a rash across his chest over the last three to four months. The patient has a past medical history of essential hypertension, hyperlipidemia, osteoarthritis of the knee, chronic gastroesophageal reflux disease (GERD), supraventricular tachycardia, status post prostate cancer, and restless legs syndrome. During his initial evaluation, he was found to have a pruritic, erythematous, papular rash most notably along his upper trunk and chest. The patient utilized multiple lotions, emollients, and anti-itch creams with minimal relief of his symptoms and presentation. Following a referral to Dermatology, a biopsy of the rash was conducted, which revealed intraepidermal acantholysis, the hallmark finding for a diagnosis of Grover's disease. Subsequently, he was treated with a topical triamcinolone acetonide 0.1% cream for 14 days. This study details a case of Grover's disease along with potential comorbidities and contributing factors in order to further understand the pathogenesis and etiology of this relatively rare condition.