  In this paper, we construct the rotating Janis-Newman-Winicour (JNW) naked
singularity spacetime using Newman-Janis Algorithm (NJA). We analyse NJA with
and without complexification methods and find that the energy conditions do
satisfied when we skip the complexification step. We study the shadows cast by
rotating JNW naked singularity and compare them with the shadows cast by the
Kerr black hole. We find that the shadow of the rotating naked singularity can
be distinguished from the shadow of the Kerr black hole. While we analyse the
precession of timelike bound orbits in rotating JNW spacetime, we find that it
can have a negative (or opposite) precession, which is not present in the Kerr
black hole case. These novel signatures of the shadow and orbital precession in
rotating JNW naked singularity spacetime could be important in the context of
the recent observation of the shadow of the M87 galactic center and the stellar
dynamics of `S-stars' around Milkyway galactic center.
