Hitler, but only with a guarantee that nobody will take his place.
Go back to see the Beatles at the Cavern Club or Buddy Holly, Richtie Valens and Big Bopper at their last performance?
American Pie, baby. 
Burpees or mountian climbers for two minutes?
Wow, guess I stumped you, huh? Okay, let’s try this.
Run a mile or swim a mile?
At my age, probably better to run a mile.
See Arrival or Fantastic Beasts?
Both are on my list but I’ll see Fantastic Beasts first.
Spend an hour coloring in a coloring book or an hour working on a jigsaw puzzle?
Not terribly keen on either, but I guess I’ll go with the coloring book.
Mostly wear red clothes or blue clothes?
Blue. That means I can wear my jeans.
Wrapping presents or sticking them in gift bags?
2 seconds vs. 2 minutes? I say gift bags.
have your bedroom perpetually smell like wet paint or new tires?
New tires. Wet paint would make me woozy after awhile.
Have your significant other smell for a month of gasoline or vanilla?
I love 'em both.
Vanilla. I’d be constantly worried about open flames otherwise.
Never again be able to smell gasoline or vanilla?
Um, never smell gasoline?
Eat a warm cookie, or be poked in both eyes with a red hot poker…
Cookie
Spend a day with Cookie Monster or with Kermit an Miss Piggy?
Miss Piggy, though abrasive at times, possesses something beyond the rudimentary communications skills demonstrated by the blue furry one. The pig wins.
spend eternity flying around clouds (or a city of gold if that suits you better) wearing a robe and playing a harp, or spend eternity being serviced by houris?
serviced by Houris of course
Would you rather live in the wilderness of Alaska or the beaches of Hawaii?
I’ve been in both places, and have little hesitation in picking Hawaii.
Stay home or go to a Christmas Eve church service?
Christmas Eve church service, every time.
Spend 3 hours in a pointless board meeting, or attempt to explain why “fake news” is a problem to a Deplorable?
It’s a waste of 3 hours either way, I’d just as soon NOT spend it with the Deplorable.
Spend all afternoon making cookies with a 6-year-old, or reading a book?
Depends on the six-year-old, but not knowing more than what you wrote, gimme a book.
Hop in a time machine to visit a particular grandmother, or grandfather, of yours for a day in their youth?
I’ll go with visiting grandma for a day in her youth (as opposed to grandpa - I dunno the choice thing seemed a little nebulous here)
Would you rather: eat, drink, or be merry? (that’s three choices, I know, but you’re an adaptable lot)
Be merry. Don’t need food or drink for that (although it never hurts).
Have a distractingly sexy dentist or eye doctor?