1. A confectionery candy that is on the end of a stick.

2. Fun.
A lollipop emoji ate a lollipop
by JulianDB December 14, 2016
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Person 1: "I'm not going to school tomorrow."
Person 2: "LUCKY!!!"
Person 1: "...I'm going to a funeral..."
Person 2: "Lollipop?!"
by Beckster09 June 19, 2009
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1. a form of candy on a stick.

2. a penis.

3. a wack ass song made by some pussy ass wannabe gangster named lil wayne who single handedly killed hip hop. He also stole the title from Snoop Dogg like most of the time he does. Dont like to hate on people but I mean, EVERY WHERE I GO somebody is riding his dick, if he has a dick.
1. WOW this lollipop tastes so good!

2. *sex sounds* oh yeah baby, now lick the lollipop *cums*

3. *Lil Wayne in Concert*

Lil Wayne: She l-l-l-l-licked me like a lollipop

Real Hip Hop fan: Shut the fuck up, the only pussy ur gonna get is birdman's, go suck a dick. You cant rap, a 5 year old could spit better lyrics then you ever will. You know why everyone is riding your dick? Because you sell records to a bunch of spoiled rich kids and a bunch of teenage girls who think your hot even though you look like my dog's ass. I actually should apologize to my dog's ass.

Lil Wayne: *cries and runs off the stage*

Concert host: Ok, Lil Wayne got off stage so now lets welcome, the renegades, JAY-Z AND EMINEM! MAKE SOME NOISE!

*Jay-Z and Eminem start to perform Renegade.*

Real Hip Hop fan: Ok this is more like it.
by The Man3455 August 01, 2009
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A Lollipop is used to describe a girl or guy who was a pretty face but a mediocre/plain body. It is the opposite of "paper bag".
Guy#1: Dudes, what do you think of that chick over there?
Guy#2: She's got a cute face.
Guy#3: Yeah, she's a total lollipop.
by Junebugg124 September 11, 2011
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