Several tumors arise from different structures within the mediastinum. Although each type of mediastinal tumor has a predilection for a specific compartment, the progression of growth from one compartment to another can occur. The anterior mediastinum is the site of several tumors that pose interesting diagnostic and therapeutic challenges to thoracic surgeons. The anterior mediastinum is the seat of the majority of neoplastic growths within the mediastinum. Thymomas and lymphomas are the most common pathologies of the anterior mediastinum. Tumors of mesenchymal origin (hemangioma, lymphangioma, lipomas) and their malignant counterparts may occur in any of the mediastinal compartments. Less common tumors of the anterior mediastinal compartment are ectopic thyroid and parathyroid tumors, germ cell tumors, mesenchymal origin tumors, hemangiomas, and cervicomediastinal hygromas. Most of the mediastinal growths usually remain clinically silent until they become large and cause compressive symptoms. Here, we present a case series of five anterior mediastinal tumors consisting of solitary benign teratoma, fibrous benign tumor, malignant fibrosarcoma, hamartomatous chondroma, and malignant thymoma.