By the mid-19th century, 20–40,000 Indian men and women of all classes had traveled to Britain. All left oral accounts that have not survived. But among the notable few who represented themselves directly in written sources (in Persian, Urdu, Nepali, or English), the entangled lives of Sake Dean Mahomet (1759–1851) and David Ochterlony Dyce Sombre (1808–1851) have proved engaging, challenging, and fruitful to study. Born only 600 miles apart in north India, they created dramatically different careers. Mahomet transformed himself from camp follower in the East India Company’s Bengal Army, to early self-published autobiographer in Cork, Ireland, to failed restaurateur in London, to famous bathhouse keeper and “Shampooing Surgeon” for the British royal family in seaside Brighton. Dyce Sombre went from heir apparent to a doomed princely state near Delhi, to wealthy but exiled traveler in southeast Asia and China, to first Member of the British Parliament who was Asian (and the second non-white), to notorious legal lunatic who vainly self-published an autobiographical book and fought judicially to disprove his insanity. Individually and together, their transcultural lives present distinct challenges and also insights for today’s biographer, due both to multifarious and often contradictory source materials and also to inherent cross-cultural interpretive issues.