A retractable lamp assembly is provided for illuminating at least a portion of a work surface from a wide range of heights and angles by way of extendable shafts and pivot joints. The lamp may be stowed in a retracted or lowered configuration when not in use, in which a substantial portion of the extendable structure is stowed inside of a housing that is located substantially below the work surface, to provide a generally unobtrusive configuration. An upper cover serves as a light reflector when the lamp is in use, and may serve as a cover positioned at or near the work surface when the lamp is stowed. Optionally, the lamp assembly includes include power and data and wire management capabilities for use at the work surface.