The interplay between cancer and obesity is multifactorial and complex with the increased risk of cancer development in obese individuals posing a significant threat. Obesity leads to the upregulation or hyperactivation of several oncogenic pathways in cancer cells, which drives them towards a deleterious phenotype. The cross-talk between cancer and obesity is considered a large contributing factor in the development of chemotherapeutic drug resistance and the resistance to radiotherapy. The link between obesity and the development of cancer is so strong that a medication that demonstrates effectiveness against both conditions would serve as an essential step. In this context, anti-obesity medications provide a worthy list of candidates based on their chemo-preventive potential and chemotherapeutic properties. The current study focuses on exploring the potential of anti-obesity medicines as dual anticancer drugs. These medications target several key signaling pathways (e.g., AMPK, PI3K/Akt/mTOR, MAPK, NF-κB, JNK/ERK), which prove to be crucial for both cancer growth and metastases. Some of these drugs also play an important role in attenuating the signaling and cellular events which incite cancer-obesity cross-talk and demonstrate efficient counteraction of neoplastic transformation. Thus, this review highlights a comprehensive view of the potential use of anti-obesity medicines to treat both cancer and obesity for patients exhibiting both comorbities.