The USS Lollipop was the name of a fictional starship that Commander William T. Riker claimed he served on in a ruse he devised in 2364.

During a visit to Minos in 2364, Riker was approached by a holographic duplicate of captain Paul Rice of the USS Drake and questioned about his ship, which Rice believed (correctly) to be the USS Enterprise-D.

Riker responded that Rice was incorrect, and that "the name of my ship is the Lollipop." When Rice did not recognize the name, Riker told him that "It's just been commissioned. It's a good ship." Rice pressed on, undeterred and taking this obviously absurd information at face value, further asking Riker "What's the armament on the Lollipop?", at which point, Riker, who was annoyed with the ruse, responded only with the unqualified quantities "Ten" and then "Six", which the hologram was unable to comprehend.

Once Riker proved to the hologram that it was indeed not Rice, it reverted into the form of an Echo Papa 607 system drone, before firing on Riker, encasing him in an "energy field". (TNG: "The Arsenal of Freedom")

The name of this "starship" and Riker's description of it was a joke, referring to the song On the Good Ship Lollipop. (Star Trek: The Next Generation Companion 2nd ed., p. 54) [1]