The breakup pathway of Rayleigh fission of a charged drop is unequivocally demonstrated by continuous, high-speed imaging of a drop levitated in an AC quadrupole trap. The experimental observations consistently exhibited asymmetric, subcritical Rayleigh breakup with an upward (i.e., opposite to the direction of gravity) ejection of a jet from the levitated drop. These experiments supported by numerical calculations show that the gravity induced downward shift of the equilibrium position of the drop in the trap causes significant, large amplitude shape oscillations superimposed over the center-of-mass oscillations. The shape oscillations result in sufficient deformations to act as triggers for the onset of instability below the Rayleigh limit (a subcritical instability). The concurrently occurring, center-of-mass oscillations, which are out of phase with the applied voltage, are shown to lead to an asymmetric breakup such that the Rayleigh fission occurs upwards via the ejection of a jet at the pole of the deformed drop. As an important application, it follows by inference that the nanodrop generation in electrospray devices will occur, more as a rule rather than as an exception, via asymmetric, subcritical Rayleigh fission events of microdrops due to inherent directionality provided by the external electric fields.