Did the Wii ever outsell the Xbox 360 despite being more expensive?

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Yes, in 2008 and 2009 before Wii reduced its price to where it actually equaled the lower 360 price. Even at the same price it continued to outsell 360 for quite some time until Wii simply continued its YOY declines and 360 remained even or gained with the launch of Kinect in 2010.