A toy skateboard assembly comprising a deck having a first end, a second end, an upper surface, and a lower surface, characterized in that it comprises: a pair of non-motorized truck assemblies (110, 120) configured for attachment to the lower surface of the deck, each of the non-motorized truck assemblies (110, 120) having a pair of freely rotatable wheels, and wherein the pairs of wheels each extend transversely to a longitudinal axis of the deck when attached; a motorized truck assembly configured for attachment to the lower surface of the deck, the motorized truck assembly comprising at least (i) a battery, (ii) a processor, (iii) a receiver in communication with the processor, and (iv) a pair of motors, each motor separately controlling a motor-controlled wheel, of a pair of motor-controlled wheels, and wherein said receiver is configured to receive signals to control the movement of the pair of motor controlled wheels; a first configuration, defined by having the pair of non-motorized truck assemblies (110, 120) separately attached to the lower surface proximate to the first end and second end, and wherein the upper surface defines a finger engaging region for a user's fingers to engage and move the toy skateboard; and a second configuration, defined by removing one of the non-motorized truck assemblies and attaching the motorized truck assembly to the lower surface in replacement thereof, such that the motor-controlled wheels are proximate to one of the front end or rear end while one of the pair of the non-motorized wheels remain attached proximate to the other end, and wherein movement of the toy skateboard is controllable by the processor in response to said signals. a pair of non-motorized truck assemblies (110, 120) configured for attachment to the lower surface of the deck, each of the non-motorized truck assemblies (110, 120) having a pair of freely rotatable wheels, and wherein the pairs of wheels each extend transversely to a longitudinal axis of the deck when attached; a motorized truck assembly configured for attachment to the lower surface of the deck, the motorized truck assembly comprising at least (i) a battery, (ii) a processor, (iii) a receiver in communication with the processor, and (iv) a pair of motors, each motor separately controlling a motor-controlled wheel, of a pair of motor-controlled wheels, and wherein said receiver is configured to receive signals to control the movement of the pair of motor controlled wheels; a first configuration, defined by having the pair of non-motorized truck assemblies (110, 120) separately attached to the lower surface proximate to the first end and second end, and wherein the upper surface defines a finger engaging region for a user's fingers to engage and move the toy skateboard; and a second configuration, defined by removing one of the non-motorized truck assemblies and attaching the motorized truck assembly to the lower surface in replacement thereof, such that the motor-controlled wheels are proximate to one of the front end or rear end while one of the pair of the non-motorized wheels remain attached proximate to the other end, and wherein movement of the toy skateboard is controllable by the processor in response to said signals.