Steal My Sunshine features Len and the group's friends are shown relaxing together and riding on skis, scooters, and go-karts. The video was shot Daytona Beach, Florida, and the scenes were shot without a script or storyboard. Motorrad, whose scooters were included in the music video, later held a promotion giving away scooters of the same model. At the 1999 MuchMusic Video Awards, "Steal My Sunshine" won awards for "Best Video", "Best Pop Video", and "Favourite Canadian Video".

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