I’ve never made it past three.
Martyr #7
On a rainy day about 25 years ago, I licked an orange tootsie pop well over 4000 times… … (I kept track with my new calculator). Now my tongue was smaller and my guess is that the pop was larger, so keep that in mind if you decide to try this yourself and decide to question my statistics.
Anyway, the doorbell rang and I went to answer it… setting down my almost conquered pop… only to come back to find that my dog had discovered it and had his way with the tootsie part. Heartsick, numb, and orange-tongued, I went back to my room.
To this day, I still have never made it without biting. I should have asked Mr. Owl.
You bring up some good points Wiggum…
The answer is probably different for different people based upon tongue size, saliva production, licking techniques, and irregularities in the size of the pops themselves…
Martyr #7
One… Two… Three…
CRUNCH
Three.
Yer pal,
Satan
It takes me 250 licks. Then again, I have a big tongue. 
Smile, it makes people wonder what you are thinking.
Fun with HTML (tutoral)
Give someone an F.U.
I used to take between 95 and 100 licks, but that was all in the same spot. Would the lick have to be all the way around? Or is licking it in one spot an acceptable method of getting to the Tootsie Roll center?
Please refrain from non-Tootsie Roll connotations involving the licking. Thank you.
Jeremy…
I can think of no more stirring symbol of man’s humanity to man than a fire engine - Kurt Vonnegut
You got me on a technicality there. I guess I didn’t specify. I was thinking of the entire removal of the hard candy coating though…
Martyr #7
Martyr#7! Wow! This has to be the dorkiest topic I’ve come across in a long time.
That’s classic! Good job.
Who actually licks Tootsie Pops? Like with all other lollipops, I just prefer to stick them in my mouth and be done with it.
Pertaining to this topic, though, I remember reading about some researchers somewhere who actually did a study on this. The average number of licks per Tootsie Pop was some ridiculous number hovering around 2,000. No word as to whether there were other statistics based on flavor or biting tendencies.
BTW, the ads I’ve seen for Tootsie Pops lately have royally sucked. Bring back Mr. Owl, dammit!
You can get to the toosie center with zero licks. Just park it inside your cheek until it dissolves. This could take days, but if this type of thing is worth the research, you’ve got the time.
Of course, your teeth may be the first to go.
Only reason I did was because Mr. Owl said it took 3 licks, and I wanted to prove it for myself. Otherwise, its firmly planted between my teeth and my cheek and it dissolved there until I bite the foolish thing.
Jeremy…
I can think of no more stirring symbol of man’s humanity to man than a fire engine - Kurt Vonnegut
Heh.
When I was a kid I actually kept count and then wrote them a letter to tell them my answer, somehow thinking I’d get famous or something (I think I was 8 or 9 at the time). I got a form letter back congratulating me on my efforts. I was very disappointed.
I don’t remember how many it took me, though.
“It says, I choo-choo-choose you. And it’s got a picture of a train.”
– Ralph Wiggum
When I was 14 I took an average of 678 licks (out of three times) to get to the center of a tootsie pop. I hate tootsie rolls but the rest of the lollipop is good.
Hugs
Sqrl
Move over Satan. 
Now there’s something meatier. http://smallwonder.simplenet.com/COC.html
Get this: ( True story, just happened on Monday night). When the US Secret Service does a sweep using it’s Bomb Squads, and dogs, to " lock up " an area prior to the arrival, or passing through of the President, they leave…Tootsie Pops for the people who they have checked. I was stunned. Apparently, this is done with some regularity. I cannot imagine why, but when I returned to the “area” where they had just swept, one guy had a fistfull of them, and said, “Compliments of the Secret Service”.
Strange world.
Cartooniverse 
" If you want to kiss the sky, you’d better learn how to kneel "
Cartooniverse:
The suckers probably had truth serum on them… Or a microchip which would get into your body for all of your movements to be tracked… or…
Well, that’s enough fodder for the conspiracy buffs!
Yer pal,
Satan
Satan said:
Or you may have accidentally hit it on the nose. The Secret Service was sending a message by giving these out: “Suckers!”
To answer th op’s question, the last Tootsie roll toostie pop I had was two years ago and bit into it, cracked and lost a filling and needed a root canal. Does anyone have Mr. Owl’s address so I can forward him the bill?
[[One… Two… Three…
CRUNCH
Three.]] Satan
That’s what I answered when this was the trivia question at my local deli, but they refused to pony up the medium coffee, on the grounds that the answer was, “the world may never know.”
I was mildly indignant.
I was watching Jenny Jones once; don’t remember the subject, but one basketball-breasted woman on stage was named Lollipop. An audience member got up and asked her “How many licks does it take to get to the center of one of them things?”