Let w = speed of bug and N = ratio of car speed/bug speed = 100. Paint N+1 equally spaced stripes on the rubberband. When the bug is standing on one stripe, the next stripe is moving away from him at a speed slightly < w (relative to him). Since he is walking at w, clearly the bug can reach the next stripe. But once he reaches that stripe, the next one is only receeding at < w. So he walks on down to the car, one stripe at a time.

The bug starts gaining on the car when he is at the next to last stripe.

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