I did it… pls enjoy

Product Placement
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@s1ncl41rr
I did it… pls enjoy
His arms are so—
He’s so—
Absolute baby boi 🥹
Lester is in Together(2025)!!!!!!
More of my HC’s for The Sinclair Brothers!
Vincent
He actually enjoys driving, but Bo never trusted him to drive alone, (since he’s missing half of his peripheral vision) which is why Bo got mad when he brought back Paige and Blake’s bodies by himself
He isn’t a smoker, but every couple of months he will steal a cigarette or two from Bo (He’ll wait until Bo gets drunk and passes out, so he can gaslight Bo into thinking he smoked extra and just doesn’t remember)
Although he doesn’t smoke tobacco, he found himself taking weed from stoner victims, He also took a weed pipe from another victim. He only smokes if he’s depressed, after an argument with Bo, or if he’s super unmotivated to sculpt or to create any art in general
He takes early morning (4-6 AM) walks, and only takes night walks if he’s stalking victims at the campsite
He’s a slight insomniac, only sleeping when he starts stumbling or not thinking coherently. He cat naps more than he sleeps
He’s Demisexual+Pansexual, he doesn’t know it though because he’s never learned labels, he just knows he’s into whoever loves him
(Slight NSFW) He hates masturbating, it makes him feel awkward and weird. He’s 100% celibate by all means
Bo
Growing up, he actually enjoyed being around Vincent most days, but (yet again) jealousy got in the way as they got older
As dangerous and crazy as he is, he would kill if it meant to protect a minor. 21+ victims only
He joked (bullied) to Vincent about being “identical” when he got his scar on his face (I know it’s Brian’s scar, but for the HoW universe, it’s ironic)
He will drink anything, but water (this might be canon)
He use to go to arcades as a kid/teen, but stopped going when his mother insisted (nagged) that he should take Vincent with him
As much as he loves cars, he only works on them to give himself a feeling of purpose
He’s a pumpkin pie kind of guy (rhyme unintended)
Lester
If he ever needs to cry to someone, he never thinks twice about going to Vincent. Every time he opens up to Bo, he gets insulted for being a, “crybaby”
He use to work on cars with Bo when their parents were still alive. He started picking up roadkill and pelting when Bo became distant
He loves SpongeBob, I don’t think I need to elaborate, he just looks like a SpongeBob watcher
Because he’s alone on the road all the time, he picked up on singing. He’s definitely not the best, but he’s ironically good
He swore to himself that he would never hurt a soul, or to ever help his brothers, but he still has it in him if need be (maybe canon?)
Unlike Bo, he actually drinks water, but only because it’s the only free drink he can find while out on the road (if he feels like his body needs it, at least)
Despite how “happy-go-lucky” he makes himself out to be, he’s extremely lonely, which is why he got so offended when Carly and Wade got uncomfortable
Lester and I twinning fr🥹 I love SpongeBob
More of my HC’s for The Sinclair Brothers!
Vincent
He actually enjoys driving, but Bo never trusted him to drive alone, (since he’s missing half of his peripheral vision) which is why Bo got mad when he brought back Paige and Blake’s bodies by himself
He isn’t a smoker, but every couple of months he will steal a cigarette or two from Bo (He’ll wait until Bo gets drunk and passes out, so he can gaslight Bo into thinking he smoked extra and just doesn’t remember)
Although he doesn’t smoke tobacco, he found himself taking weed from stoner victims, He also took a weed pipe from another victim. He only smokes if he’s depressed, after an argument with Bo, or if he’s super unmotivated to sculpt or to create any art in general
He takes early morning (4-6 AM) walks, and only takes night walks if he’s stalking victims at the campsite
He’s a slight insomniac, only sleeping when he starts stumbling or not thinking coherently. He cat naps more than he sleeps
He’s Demisexual+Pansexual, he doesn’t know it though because he’s never learned labels, he just knows he’s into whoever loves him
(Slight NSFW) He hates masturbating, it makes him feel awkward and weird. He’s 100% celibate by all means
Bo
Growing up, he actually enjoyed being around Vincent most days, but (yet again) jealousy got in the way as they got older
As dangerous and crazy as he is, he would kill if it meant to protect a minor. 21+ victims only
He joked (bullied) to Vincent about being “identical” when he got his scar on his face (I know it’s Brian’s scar, but for the HoW universe, it’s ironic)
He will drink anything, but water (this might be canon)
He use to go to arcades as a kid/teen, but stopped going when his mother insisted (nagged) that he should take Vincent with him
As much as he loves cars, he only works on them to give himself a feeling of purpose
He’s a pumpkin pie kind of guy (rhyme unintended)
Lester
If he ever needs to cry to someone, he never thinks twice about going to Vincent. Every time he opens up to Bo, he gets insulted for being a, “crybaby”
He use to work on cars with Bo when their parents were still alive. He started picking up roadkill and pelting when Bo became distant
He loves SpongeBob, I don’t think I need to elaborate, he just looks like a SpongeBob watcher
Because he’s alone on the road all the time, he picked up on singing. He’s definitely not the best, but he’s ironically good
He swore to himself that he would never hurt a soul, or to ever help his brothers, but he still has it in him if need be (maybe canon?)
Unlike Bo, he actually drinks water, but only because it’s the only free drink he can find while out on the road (if he feels like his body needs it, at least)
Despite how “happy-go-lucky” he makes himself out to be, he’s extremely lonely, which is why he got so offended when Carly and Wade got uncomfortable
the only man thats been on my mind recently…
I've been thinking about this bit of the blooper reel for a while and it's. Damon as Lester, of course, but it kinda?? solidifies the way that Lester is written and perceived on here for me. Damon's personality is shining through with the Louisiana accent and if you were to take this as extra Lester dialogue, it fits the narrative that he has in headcanons and fics where he's sweet, kind, encouraging. the praise ?? fits perfectly.
also ofc all credits to the how team, this clip isn't mine
“smoking kills!”
↳damon herriman in the short film the hitch (2001)
He's so cute and hot
My contribution to this trend
I seriously need to draw him more!!!
I’m in the middle of drawing Vincent as well 🤭
Lester's weird and definitely very freaky but it's ok because so am I
Dating Lester Sinclair headcanons, because there ain’t enough appreciation for him!
- Lester is actually The Best boyfriend .
- If you don’t mind the smell of roadkill, that is .
sappy Vincent art under the cut.
CW self harm/scars
Lester is indeed passive and doesn't fool anyone 🫢
He tries his best to act tough
Growing up the youngest (and smallest) meant he was always beat up on, made fun of, and just generally not taken seriously
So he does have a bit of a chip on his shoulder when it comes to dealing with his brothers
But with you- he's always soft. He doesn't carry the "tough guy" persona well- you see right thru it
He loves making you happy, giving you what you want, letting you take control
Because you do so in a loving way-
As someone who grew up having to take care of himself completely: he's never experienced someone who cares for him in a nuturing or loving way
It feels so nice to let someone else be in charge
I'd spoil him rotten
My sweet Vinny who has never done anything wrong
Lester Sinclair + frogs hcs
Okay thanks to @coppasulfate I am now OBSESSED with the idea of Lester loving frogs. hes a frog boy at heart and nothing can change my mind.
Since he was left alone a good chunk of his childhood he had to make his own fun, and one way he did that was going to the nearby creek and catching frogs.
Baby Les spent so much time just crouched at the side of the creek wearing his bright green froggy rain boots trying to spot some frogs in the water.
He refuses to leave his hunt empty handed. He will catch a frog, and he will take it home, no matter how long it takes.
Omg Les and I would get along well🥹 I love frogs
House of Wax in the big ‘25? more likely than you think
idk if it even ended up looking like Lester i struggle a lot with drawing non-generic faces, also i drew it from memory😭🙏
MY MAN MY MAN MY BABYY