New anticancer therapies have improved patient outcomes but associated dermatologic adverse events (AEs) may cause morbidity and treatment discontinuation. A comprehensive estimation of associations between cancer drugs and skin AEs is lacking. This study utilized the FDA's Adverse Event Reporting System (FAERS) database (January 2013-September 2022), with 3,399,830 reports involving 3,084 drugs and 16,348 AEs. A nearest neighbor matching model was employed to select 10 controls for each case report, utilizing the cosine similarity of demographic and AE severity factors to minimize false positives/ negatives. There were 10,698 unique anticancer drugs (n=212) to skin AE (n=873) pairs, of which 676 had significant Reporting Odds Ratios (ROR) >1, comprising 113 drugs and 144 AEs. The minimum ROR was 1.25, and 50% of associations displayed a ROR >10. The most common were rash (51 agents) and dry skin (28 drugs). Methotrexate induced the most distinct AEs (34), then mechlorethamine (33), and vemurafenib (24). Targeted therapies accounted for 49% of pairs, cytotoxic chemotherapies for 35.9%, and immunotherapies for 11%. 113 anticancer drugs were identified as significantly associated with skin AEs, most frequently rash and dry skin. Data are likely underreported but enable quick post-marketing identification of skin toxicity signals.