#ruby and oscar
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Because I’m sick and stuck in bed and bored:


Edit: For obvious reasons, Ironwood also qualifies for genocide and Maria also qualifies for “hoes mad”
#rwby#rwby memes#ruby rose#weiss shnee#blake belladonna#yang xiao long#rwby sun wukong#neptune vasilias#penny polendina#maria calavera#oscar pine#pyrrha nikos#jaune arc#nora valkyrie#lie ren#emerald sustrai#mercury black#ozpin#qrow branwen#ilia amitola#james ironwood#greenlight volume 10#greenlight rwby volume 10#greenlightvolume10#crwby
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I feel stupid I just realized that both Ruby and Oscar have little in the title of their stories their based on
I always forget that Ruby story is called Little Red Riding Hood and not just Red Riding Hood
Lol, it's alright anon-chan XD Coincidentally, this squiggly Pinehead and Rosegardener didn't make that connection either until you brought it up so figuratively we're in the same boat m'fam.
I guess that's another connection to add to the growing list of why Ruby and Oscar work well together. They are our two smaller, more honest souls after all.
LMS (2025)
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Please notice the smile and breath that Ruby releases once Oscar is safe and sound.
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HAPPY PRIDE (a year and a half late but it's fine)
#rwby#ruby rose#oscar pine#rosegarden#memes#fanart#finally i can take this out of the wip folder#i'm more of a demi aroace ruby truther but#STILL COUNTS
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#rwby#rwby fanart#rwby shitpost#rwby sun wukong#yang xiao long#ruby rose#ruby rose rwby#blake belladonna#weiss schnee#oscar pine#ugh i hate making posts with a lot of characters#why am i tagging all of these guys#nora valkyrie
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#cartoon#cartoonstyle#manga#fanart#comic#rwby#yang xiao long#ruby rose#weiss schnee#blake belladonna#jean d arc#nora valkyrie#lie ren#oscar
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"Ruby, you-" "Oscar, you-"
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they are the sillies of all time
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A bird and his babies
Any guy can be a babygirl, but it takes a man to be a single mother
#rwby#qrow branwen#ruby rose#yang xiao long#weiss schnee#blake belladonna#jaune arc#nora valkyrie#lie ren#oscar pine#mine#my art
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predecessor / successor
#rwby#ruby rose#rwby fanart#oscar pine#rwby rosegarden#?kindaidkisaidso#rwby rg#summer rose#professor ozpin
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"...because you did start something."
#digital art#rwby#rwby9#rwbyfanart#fanart#oscar pine#ruby rose#Weiss Schnee#jaune arc#blake belladonna#yang xiao long#winter schnee#robyn hill#qrow branwen#nora valkyrie#lie ren#penny polendina
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Stuff that piled up that I forgot to post
#my art#rwby#qrow branwen#ruby rose#emerald sustrai#oscar pine#emerald city gives me brain worms btw I have a bunch of art ideas for them#been in a silly mood lately so some goofier art until further notice#Qrow has no idea how to be supportive but him winging has worked out so far
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Oscar's Undisclosed Birthday
So…m’good friend @jealouscartoonist just shared with me this new cameo from Miles talking about Oscar’s birthday and this squiggly Pinehead is just all smiles now.
Listening to Miles describe with such pure joy an ideal birthday for Oscar was the big kick of serotonin that I didn’t know I needed until I listened to the whole thing. Shoutout to whoever this Sarah person who sent in this cameo is. Thank you for doing the Pinehead community another solid.
This just makes me more salty that Oscar was NEVER EVER added to RWBY Chibi since Miles’ description of “Oscar’s Undisclosed Birthday” is just perfect for as a concept for another wholesome episode of the series that’s Oscar-worthy. Even calling the episode “Oscar’s Undisclosed Birthday” seems perfect as an appropriate title.
Miles made my night with this cameo. It’s everything I wanted for how Oscar would spent his special day (minus actually GIVING US HIS CANON birthday) and I love how Miles dropped more cute tidbits about Oscar as a character too.
Oscar’s favourite breakfast is waffles (and how his big sis Nora would actually make a big pile for him).
Apparently Oscar has trouble sleeping sometimes because of Oz being in his head so Ren gifting him a pair of headphones to drown out the voice of the old headmaster would be useful. Miles basically admitted that Oz is a chatterbox. Makes me think of that “Brain Before Sleep” meme only replace the brain with Oz XD That’s the first thing that popped into my head. Thanks for that imagery Miles.
Oscar loves going to the movies especially Spruce Lee (LOL) films which he shares in common with Jaune and that’s how they bond.
Yang would take Oscar on a fun day at the amusement park where they’d ride all the rides that he’s now tall enough to ride (another LOL from me because they always gotta poke fun that my little prince is a short king)---that would be a thing Yang would do and I cannot picture Oscar turning that down since, in the words of Ruby, Oscar is braver than he thinks and we have seen moments of Oscar being more daring than he looks so he totally would not pass up an opportunity to ride all the rides especially if Yang is the one pushing him to do it.
So the “Girl Who Fell Through the World” is confirmed to be Oscar’s favourite childhood fairytale---and Blake getting him a second edition of it is cute being the book-worm that she is.
I also love the bit with Weiss panicking about not knowing what to get Oscar so she just gives him a lumpsome of money and Oscar being floored by it since he’s never had that amount of money in his life---that fits beautifully.
And of course, gotta love how Miles saved the best gift for last. Ruby gifting Oscar a new co-op videogame that they both end up spending the rest of his birthday playing til they both crash the morning after (Oscar first) is more than a perfect way to conclude Oscar’s birthday in my Rosegarden-shipping books.
*chef’s kiss*
Didn’t even realize that Oscar liked playing videogames. Didn’t know he had them back on the farm. This just makes me think back to his reaction to Ruby’s videogame comment back in V6. Puts the whole moment in a new context for me XD
All in all, Miles made me a happy Pinehead tonight.
~LMS (2023)
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these kids and their identity issues 😔
#i beg you#please stop leaving tags on this post saying Oscar gets overwritten by Oz#its much more nuanced and complicated than that#oscar pine#Ruby rose#rwby rosegarden#fanart#rwby fanart#sketches#rwby#rosegarden
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