Background/Objectives: Sentinel Lymph Node Biopsy (SLNB) aims at identifying clinically occult nodal metastases. It is the standard staging procedure for patients with T1b to T4 primary cutaneous melanoma. Moreover, it is recommended whenever the risk of a positive SLNB is >5%, according to the National Comprehensive Cancer Network Melanoma guidelines. When considering Non-Melanoma Skin Cancer (NMSC), the SLNB could play a role in tumors that mainly spreads via lymphatics, but strong evidence is missing. In this paper, the hot topics and controversies are reviewed; Methods: A PRISMA systematic review was carried out on the PubMed (MEDLINE) library from 2004–2024, searching for studies on SLNB in NMSC; Results: Seventy articles and 6379 patients undergoing SLNB for Squamous Cell Carcinoma (SCC), Merkel Cell Carcinoma (MCC), and Porocarcinoma were included. Overall, the SLNB positivity rate in these NMSCs was 24.4%, with an SNLB detection rate of 97.6%. Specifically, the SLNB positivity rate was 12.3% for high-risk cutaneous SCC, 24.4% for anogenital SCC, 29.3% for MCC, and 30.6% for Porocarcinoma. Most papers concluded that SLNB is safe, feasible, and significant in these malignancies; Conclusions: SLNB should be discussed and offered to every patient with MCC, and it should be discussed and considered in “high risk” SCC and Porocarcinoma for staging and prognostic purposes, aiming to identify a subgroup of patients who may benefit the most from early treatments.