Anaplastic thyroid carcinoma (ATC) accounts for 5%–10% of primary thyroid malignancies. Cytodiagnosis of osteoclast-like giant cells (OLGCs) variant of ATC is very rare with only few cases reported in literature. We report a case of ATC with OLGC variant in an 85-year-old female who presented with swelling in the right lobe of thyroid and scalp nodule, which on radiological evaluation and subsequent fine-needle aspiration biopsy (FNAB) was diagnosed as ATC having numerous OLGC with metastases in skull bones. Cytologically, thyroid aspirate revealed sheets of epithelioid neoplastic cells admixed with many OLGC. Aspirate from the scalp nodule showed neoplastic cells with follicular differentiation. She also had radiological evidence of lung metastasis. Such a presentation of this rare variant being diagnosed by FNAB is rarely reported in literature and highlights the importance of this simple procedure in diagnosing and planning management of this rare condition.