Most malignant obstructive jaundice arises from primary periampullary tumors and rarely from metastatic cancer of the head and neck. A 60-year-old male was diagnosed with obstructive jaundice due to metastatic squamous cell carcinoma of the tonsil. Only 12 cases of small bowel metastasis from the head and neck have been reported. Most of them originate from laryngeal squamous cell carcinoma, and only one case reported tonsillar cancer metastasizing to the ileum. Our case is the first one, to the best of our knowledge, to illustrate tonsillar cancer with metastasis to the duodenum causing obstructive jaundice.