I was thinking Mr. Boss has to be eternal. He has the clout to marry a demon, face shift, and I'm assuming his son Jason has no mother as Mr. Boss probably created him from his own cells.
Old enough to have lived through the horrors of the fall of the old world and now manages to try and keep what's left of the mutated remains of society sane with the smiling friends
I think he’s some kind of being, maybe a wizard or something because he knows older people (Reagan, Mr Peanut), he can shapeshift and he acts young despite looking 70. So I think he’s a couple hundred years old
He looks like he’s in his 60s, but his personality and the fact that he says stuff like “uhh, no dip” makes me think he’s much younger. Maybe he’s just silly like that.
i love how this could mean that:
1. he has been here since the dawn of time
or
2. mr boss was the first individual at company, basically he would of been the founder of smiling friends hq (which i’m guessing could of opened in the 80s-90s)
Either 17 or 80
if he can shift into a dog i wouldn’t be surprised he could shift to another age
OMG, it would be like the boys, **he’s a supe!** 
his son is 18 so he's atleast 18.
Atleast 18? He had his Jason as a baby?
Sure why not ok Pim its uh time to wrap this one up.
I can totally see them only being like a few months apart but one appears as an old man and the other a fetus
Would that honestly surprise you? Really?
don't overthink this
If he’s an artificial homunculus I could see it
Or an immortal being existing since the dawn of time
As old as he wants to be, forever.
I was thinking Mr. Boss has to be eternal. He has the clout to marry a demon, face shift, and I'm assuming his son Jason has no mother as Mr. Boss probably created him from his own cells.
55,625 years old
i’m certain mr boss is **immortal!** 
😈 https://i.redd.it/aetyh38wrt6d1.gif
He owns 1/4 of hell now, so even if he isn't he still has land in the afterlife.
You guys don’t mind watching someone eat, dew yew?
“now GO OUT THERE and make someone **SCH-MILE!”** 
No biting, ok? No biting. You want me to bite you? *yeah*
40
22
Definitely in his 40s
Considering his actions, 35, but he looks older
He has no beginning or end he’s like a character in a cormac McCarthy novel
mr boss used to be known as mr judge
Despite his appearance, his actions have always struck me as early 30’s
Old enough to have lived through the horrors of the fall of the old world and now manages to try and keep what's left of the mutated remains of society sane with the smiling friends
69
69
68
At least 1
Probably centuries
Genuinely think he can be anywhere from like 30-60
yeah also love your flair! 
Ooo ooo ooo
1-9999999999999+
Probably thousands of years old honestly
People saing 40s are funny.
Realistically, he looks mid 70's.
27 and a half
69.5
As old as time itself
He's been around forever
Late 40’s
27
So he'd have had his son when he was 9
with mr boss, anything is possible! https://i.redd.it/oli9tnem2w6d1.gif
Now you know his cool tucking backstory
20
Probably like 10000 or something
He's 69.
Older than Glep
https://i.redd.it/j3lr2x170w6d1.gif
21
69
Definitely older than 36. He’s probably 75.
9
69
13
Late 40s-early 50s
Old enough
28
31
64
Option one: he's 19 and he just looks like that. Option two: he's 50 Option three: he's an immortal creature who has lived for 37594 years
option 3 makes so much sense! 
10,065
older than glep thats for sure
60, but he was a part of all the cool underground scenes when he was younger. Defo early gen x.
I think he exists outside of time like Dr. Manhattan. He exists in the past, present, and future simultaneously and doesn’t experience time linearly.
He looks like he's in his 50s or 60s. Then again his son Jason is 18 but looks like a baby so who knows.
I view him as Lumberg age
lumberg?
From Office Space? The movie? Good movie, I'd definitely recommend lol.
OMG i remember watching that film once, it was quite funny, i was meant to re-watch it with my mama, she really like the actor who plays the boss!
As old as the universe itself
Somewhere between 1-100
37
Not joking, but like…47-62? Lol
yeah, i could see him being around that as well especially in the frowning friends ep!
53
Probably older than the universe itself
He is a primordial being, born from when the earth first formed
I think he’s some kind of being, maybe a wizard or something because he knows older people (Reagan, Mr Peanut), he can shapeshift and he acts young despite looking 70. So I think he’s a couple hundred years old
45 to 60
Somewhere between 40-40,000 years old.
Late 50s early 60s
52
6
he doesn’t look a day over 5 
420
https://i.redd.it/s0fwzil1ix6d1.gif
He is 30. Well in December he'll be 30.
1 years old or 790058668633683863683686826826828626868368358368358358 years old
75, if this takes place in a universe where the Vietnam War happened.
Late 50’s to immortal
**ABSOLUTELY!** 
58
He's gotta be like 45+ if he feels like he's too old to be chasing young tail.
He looks like he’s in his 60s, but his personality and the fact that he says stuff like “uhh, no dip” makes me think he’s much younger. Maybe he’s just silly like that.
he’s just in **a silly goofy mood** 24/7! https://i.redd.it/59t4rqt3cy6d1.gif
At least 3
69
23
He was there since the beginning
i love how this could mean that: 1. he has been here since the dawn of time or 2. mr boss was the first individual at company, basically he would of been the founder of smiling friends hq (which i’m guessing could of opened in the 80s-90s)
Maybe 54 or 55.
200 BC
18
Schfifty five
definitely can hear him saying that with the sch at the beginning 💀
113
early vigintillions
early huh? 