The music video for " Strawberry Kisses " was directed by Mark Hartly . The video features Webster entering a space ship and meets up with a computer animated character called Digital Jimmy . Digital Jimmy ( DJ ) was created by Hartly , and Webster thought the idea was fantastic and when she saw the basic drawing she fell in love with him . Digital Jimmy presses a button on a remote control , which changes Webster 's outfit from a pink dress resembling her 2000 Summer Olympics opening ceremony costume , to pink crop top and pants . Webster then sings in a microphone for the first one minute of the song , starts dancing then as the song finishes she leaves the space ship and goes on another space ship ending the video . Webster stated that the back-up dancers in the video were her friends from her dance class
2000 Summer Olympics opening ceremony
2000 Summer Olympics opening ceremony
Strawberry Kisses