Example embodiments provide systems and methods for rewinding digital content during playback based on context of the digital content. A content rewind system electronically accesses digital content. A rewind trigger is detected by the system. The system analyzes the digital content to detect at least one dialog segment within the digital content. The analysis is based on context of the digital content (e.g., dialog within the digital content). The system rewinds playback of the digital content by rewinding to a starting point of a previous dialog segment.