Apple, Motorola, and Cingular launched the first iTunes phone in 2005 for $249.99 with a two-year contract. It carried up to 100 songs. The same day, Apple announced a $249 iPod nano holding 1,000 songs, turning the ROKR launch into its own comparison ad.
Sources: Apple’s ROKR announcement; Apple’s same-day iPod nano announcement.
Image: Diego Salatino / Wikimedia Commons, CC BY-SA 4.0.