Patient History A 67-year-old male presented with symptoms of mania eight days after switching from sertraline to bupropion. His past medical history included benign prostatic hyperplasia, erectile dysfunction, insomnia, and a recent diagnosis of depression. He denied previous history of depression but reported taking sertraline for premature ejaculation, an off-label use. His baseline aspartate aminotransferase (AST) was 20 U/L and alanine transaminase (ALT) was 22 U/L. Bupropion was held on admission and olanzapine 5 mg nightly was initiated to treat mania. Following six days of olanzapine treatment, his liver function tests (LFTs) were elevated (AST = 83 U/L, ALT = 105 U/L) and peaked two days later at AST being 2,024 U/L and ALT being 1,508 U/L. Other causes of LFT elevation were ruled out since no other new medications were started and the patient denied use of acetaminophen. Olanzapine was subsequently discontinued and his LFTs began to improve. His symptoms of mania resolved, and he was discharged on no psychotropic medications. Review of Literature A literature search identified 6 cases of bupropion-induced mania/hypomania and 10 cases of olanzapine-induced increased LFTs. This case will add to the limited reports regarding these adverse effects. Conclusion Possible adverse drug reactions (ADRs) were observed between the initiation of bupropion and the development of manic symptoms as well as the initiation of olanzapine and elevated LFTs. The case report also focuses on the role of pharmacy in a patient with multiple ADRs from psychotropic medications and the importance of gaining collateral information and clarifying indications of prescribed medications.