Drug rash with eosinophilia and systemic symptoms (DRESS) syndrome is a rare drug reaction that commonly presents with rash, fever, lymphadenopathy, eosinophilia, and multiorgan involvement. We present a case of this syndrome in a 31-year-old male who presented with a diffuse erythematous morbilliform rash with high fever and elevated liver enzymes. Upon history taking, the patient reported acute onset of multiple seizures that required intubation and ICU admission six weeks prior, which started 24 hours after receiving the Johnson and Johnson Janssen coronavirus disease 2019 (COVID-19) vaccine. During that hospitalization, he was given antiseizure medications Keppra (levetiracetam) and Dilantin (phenytoin), which he was eventually discharged home with. During our encounter with the patient, Dermatology was consulted and recommended punch skin biopsy, which revealed spongiotic dermatitis with subcorneal pustules along with superficial perivascular and mixed lymphocytic and neutrophilic infiltrate with dermal edema and rare eosinophils. Given these findings in conjunction with the patient's fever, elevated liver function, and cervical lymphadenopathy, the rash was consistent with DRESS syndrome or a pustular drug eruption likely secondary to phenytoin or levetiracetam. This case was eventually resolved with treatment with oral and topical corticosteroids and close outpatient follow-up with Dermatology. Prompt diagnosis and treatment of DRESS syndrome are therefore critical as the mortality rate can be as high as 10% in the setting of liver failure.