akumatsu best from all time

Time frame

akumatsu

10s akumatsu bad_id bad_twitter_id brothers buck_teeth cosplay cuphead_(game) enerunaru hat hood hoodie iyami king_dice king_dice_(cosplay) male_focus matsuno_choromatsu matsuno_ichimatsu matsuno_jyushimatsu matsuno_karamatsu matsuno_osomatsu matsuno_todomatsu osomatsu-kun osomatsu-san osomatsu_(series) parody sextuplets siblings simple_background style_parody teeth toon_(style) top_hat white_background
10s akumatsu bad_id bad_twitter_id brothers buck_teeth cosplay cuphead_(game) enerunaru hat hood hoodie iyami king_dice king_dice_(cosplay) male_focus matsuno_choromatsu matsuno_ichimatsu matsuno_jyushimatsu matsuno_karamatsu matsuno_osomatsu matsuno_todomatsu osomatsu-kun osomatsu-san osomatsu_(series) parody sextuplets siblings simple_background style_parody teeth toon_(style) top_hat white_background
>_< 10s 6+boys 6+girls :3 :d :p \m/ ^_^ adapted_costume ahoge aida_(osomatsu-san) akumatsu alternate_hairstyle animal animal_ears animal_print aqua_eyes arm_up atsushi_(osomatsu-san) bald baseball_bat black_hair blonde_hair blue_eyes blue_flower blunt_bangs bob_cut bow bowl_cut braid breasts brothers brown_hair buck_teeth camellia cat_ears cat_print chainsaw character_mask chibi chibimi chibita choroko_(osomatsu-san) cleavage closed_eyes closed_mouth colored_sclera dancing dark_skin dayoon dayoon_girl dekapan dobusu_(osomatsu-san) dual_wielding esper_nyanko everyone facial_hair facial_mark fake_animal_ears fireworks_print fish fish_print fleur-de-lis floral_print flower flower_fairy_(osomatsu-kun) folded_ponytail funuyu gender_request genderswap geta glasses glasses_boy_(osomatsu-san) glowstick grey_hair grin hair_bow hair_bun hair_flower hair_ornament hairband hairclip hashimoto_nyaa hatabou head_flag heart heart_hair_ornament heart_in_mouth highres hijirisawa_shonosuke holding holding_animal holding_fish holding_flower holding_weapon husband_and_wife hydrangea ichiko_(osomatsu-san) iyami iyayo japanese_clothes jigusou jitome jyushiko_(osomatsu-san) jyushimatsu's_girlfriend kamimatsu karako_(osomatsu-san) kimono kinchaku laughing long_hair looking_at_another looking_at_viewer looking_to_the_side low_twintails mask mask_on_head matsuno_choromatsu matsuno_ichimatsu matsuno_jyushimatsu matsuno_karamatsu matsuno_matsuyo matsuno_matsuzou matsuno_osomatsu matsuno_todomatsu motion_blur multiple_boys multiple_girls mustache no_socks obi object_on_head open_mouth osoko_(osomatsu-san) osomatsu-kun osomatsu-san osomatsu_(series) outstretched_arms pale_skin paw_print polka_dot ponytail pouch print_kimono rabi red_bow red_flower red_lips red_rose red_sclera rose sachiko_(osomatsu-san) sanematsu_(osomatsu-san) sash sextuplets sheeeh! short-haired_girl_(osomatsu-san) short_hair short_twintails siblings sidelocks simple_background single_hair_bun skull_print smile smirk striped summer_festival sunflower_print swinging teeth todoko_(osomatsu-san) tongue tongue_out triangle_mouth twin_braids twintails twitter_username variations wavy_hair weapon whisker_markings white_background yowai_totoko yukata
>_< 10s 6+boys 6+girls :3 :d :p \m/ ^_^ adapted_costume ahoge aida_(osomatsu-san) akumatsu alternate_hairstyle animal animal_ears animal_print aqua_eyes arm_up atsushi_(osomatsu-san) bald baseball_bat black_hair blonde_hair blue_eyes blue_flower blunt_bangs bob_cut bow bowl_cut braid breasts brothers brown_hair buck_teeth camellia cat_ears cat_print chainsaw character_mask chibi chibimi chibita choroko_(osomatsu-san) cleavage closed_eyes closed_mouth colored_sclera dancing dark_skin dayoon dayoon_girl dekapan dobusu_(osomatsu-san) dual_wielding esper_nyanko everyone facial_hair facial_mark fake_animal_ears fireworks_print fish fish_print fleur-de-lis floral_print flower flower_fairy_(osomatsu-kun) folded_ponytail funuyu gender_request genderswap geta glasses glasses_boy_(osomatsu-san) glowstick grey_hair grin hair_bow hair_bun hair_flower hair_ornament hairband hairclip hashimoto_nyaa hatabou head_flag heart heart_hair_ornament heart_in_mouth highres hijirisawa_shonosuke holding holding_animal holding_fish holding_flower holding_weapon husband_and_wife hydrangea ichiko_(osomatsu-san) iyami iyayo japanese_clothes jigusou jitome jyushiko_(osomatsu-san) jyushimatsu's_girlfriend kamimatsu karako_(osomatsu-san) kimono kinchaku laughing long_hair looking_at_another looking_at_viewer looking_to_the_side low_twintails mask mask_on_head matsuno_choromatsu matsuno_ichimatsu matsuno_jyushimatsu matsuno_karamatsu matsuno_matsuyo matsuno_matsuzou matsuno_osomatsu matsuno_todomatsu motion_blur multiple_boys multiple_girls mustache no_socks obi object_on_head open_mouth osoko_(osomatsu-san) osomatsu-kun osomatsu-san osomatsu_(series) outstretched_arms pale_skin paw_print polka_dot ponytail pouch print_kimono rabi red_bow red_flower red_lips red_rose red_sclera rose sachiko_(osomatsu-san) sanematsu_(osomatsu-san) sash sextuplets sheeeh! short-haired_girl_(osomatsu-san) short_hair short_twintails siblings sidelocks simple_background single_hair_bun skull_print smile smirk striped summer_festival sunflower_print swinging teeth todoko_(osomatsu-san) tongue tongue_out triangle_mouth twin_braids twintails twitter_username variations wavy_hair weapon whisker_markings white_background yowai_totoko yukata
10s 2boys akumatsu bad_id bad_twitter_id black_hair black_sclera buddha chain collar colored_sclera colored_skin dainamo earlobes fingernails grin highres kamimatsu long_earlobes male_focus multiple_boys osomatsu-san osomatsu_(series) parody pointy_ears purple_skin red_sclera sharp_fingernails sharp_teeth sharp_toenails sitting smile teeth toenails
10s 2boys akumatsu bad_id bad_twitter_id black_hair black_sclera buddha chain collar colored_sclera colored_skin dainamo earlobes fingernails grin highres kamimatsu long_earlobes male_focus multiple_boys osomatsu-san osomatsu_(series) parody pointy_ears purple_skin red_sclera sharp_fingernails sharp_teeth sharp_toenails sitting smile teeth toenails
10s 3boys akumatsu black_hair blush brothers colored_sclera crying family groping hood hoodie hug incest male_focus matsuno_ichimatsu matsuno_karamatsu messy_hair multiple_boys osomatsu-kun osomatsu-san osomatsu_(series) red_sclera siblings sweat text_focus translation_request twitter_username yaoi yutarosu
10s 3boys akumatsu black_hair blush brothers colored_sclera crying family groping hood hoodie hug incest male_focus matsuno_ichimatsu matsuno_karamatsu messy_hair multiple_boys osomatsu-kun osomatsu-san osomatsu_(series) red_sclera siblings sweat text_focus translation_request twitter_username yaoi yutarosu
10s 2boys akumatsu cat's_cradle chiyo_(shuten_dj) closed_eyes colored_sclera earlobes hood hoodie kamimatsu long_earlobes male_focus multiple_boys osomatsu-san osomatsu_(series) red_sclera size_difference sketch smile string string_of_fate
10s 2boys akumatsu cat's_cradle chiyo_(shuten_dj) closed_eyes colored_sclera earlobes hood hoodie kamimatsu long_earlobes male_focus multiple_boys osomatsu-san osomatsu_(series) red_sclera size_difference sketch smile string string_of_fate
10s 2boys akumatsu arms_behind_back black_hair colored_sclera denim earlobes enerunaru hands_in_pocket hands_in_pockets highres hood hoodie jeans kamimatsu long_earlobes male_focus multiple_boys osomatsu-san osomatsu_(series) pants red_sclera shaded_face sharp_teeth simple_background smile teeth white_background yellow_eyes
10s 2boys akumatsu arms_behind_back black_hair colored_sclera denim earlobes enerunaru hands_in_pocket hands_in_pockets highres hood hoodie jeans kamimatsu long_earlobes male_focus multiple_boys osomatsu-san osomatsu_(series) pants red_sclera shaded_face sharp_teeth simple_background smile teeth white_background yellow_eyes
10s 1girl 5boys :3 :d :o akumatsu alternate_costume atsushi_(osomatsu-san) black_dress black_footwear black_gloves black_hair black_jacket black_pants black_wings brown_hair candle chair clenched_teeth cloak collared_shirt colored_sclera crossed_arms demon demon_girl demon_horns demon_tail demon_wings dress fang fire floating formal_clothes frown gloves grey_background hairband highres horns jacket long_sleeves looking_at_viewer low_twintails matsuno_osomatsu matsuno_todomatsu middle_finger multiple_boys necktie newo_(shinra-p) object_on_head on_chair open_mouth osomatsu-kun osomatsu-san osomatsu_(series) pants plaid_clothes plaid_shirt red_background red_eyes red_necktie red_sclera red_shirt sharp_teeth shirt shoes short_twintails simple_background sitting sketch smile smoke suit sweatdrop tail teeth torn_clothes tougou_(osomatsu-kun) twintails uneven_eyes wings yowai_totoko
10s 1girl 5boys :3 :d :o akumatsu alternate_costume atsushi_(osomatsu-san) black_dress black_footwear black_gloves black_hair black_jacket black_pants black_wings brown_hair candle chair clenched_teeth cloak collared_shirt colored_sclera crossed_arms demon demon_girl demon_horns demon_tail demon_wings dress fang fire floating formal_clothes frown gloves grey_background hairband highres horns jacket long_sleeves looking_at_viewer low_twintails matsuno_osomatsu matsuno_todomatsu middle_finger multiple_boys necktie newo_(shinra-p) object_on_head on_chair open_mouth osomatsu-kun osomatsu-san osomatsu_(series) pants plaid_clothes plaid_shirt red_background red_eyes red_necktie red_sclera red_shirt sharp_teeth shirt shoes short_twintails simple_background sitting sketch smile smoke suit sweatdrop tail teeth torn_clothes tougou_(osomatsu-kun) twintails uneven_eyes wings yowai_totoko
10s 2boys ;) akumatsu arm_on_another's_shoulder bad_id bad_twitter_id black_hair circle colored_sclera contrapposto cowboy_shot crossed_arms denim earlobes fingernails grey_background grin highres hood hoodie jeans kamimatsu long_earlobes male_focus messy_hair money_gesture multiple_boys o2_(o2mm) one_eye_closed osomatsu-san osomatsu_(series) pants pointy_ears red_sclera sharp_fingernails simple_background smile standing swept_bangs v yellow_eyes
10s 2boys ;) akumatsu arm_on_another's_shoulder bad_id bad_twitter_id black_hair circle colored_sclera contrapposto cowboy_shot crossed_arms denim earlobes fingernails grey_background grin highres hood hoodie jeans kamimatsu long_earlobes male_focus messy_hair money_gesture multiple_boys o2_(o2mm) one_eye_closed osomatsu-san osomatsu_(series) pants pointy_ears red_sclera sharp_fingernails simple_background smile standing swept_bangs v yellow_eyes
10s 3boys ;p ^^^ akumatsu bad_id bad_twitter_id black_hair colored_sclera denim heart heart_in_mouth hood hoodie jeans kahadu kamimatsu male_focus matsuno_osomatsu multiple_boys one_eye_closed osomatsu-kun osomatsu-san osomatsu_(series) pants red_sclera scissors sharp_teeth shears tearing_up teeth tongue tongue_out yellow_eyes
10s 3boys ;p ^^^ akumatsu bad_id bad_twitter_id black_hair colored_sclera denim heart heart_in_mouth hood hoodie jeans kahadu kamimatsu male_focus matsuno_osomatsu multiple_boys one_eye_closed osomatsu-kun osomatsu-san osomatsu_(series) pants red_sclera scissors sharp_teeth shears tearing_up teeth tongue tongue_out yellow_eyes
33140410 ahoge akumatsu black_hair blue_hoodie fingernails green_hoodie highres hood hoodie kamimatsu long_earlobes matsuno_choromatsu matsuno_ichimatsu matsuno_jyushimatsu matsuno_karamatsu matsuno_osomatsu matsuno_todomatsu osomatsu-san osomatsu_(series) pink_hoodie purple_hoodie red_hoodie ribbon-trimmed_sleeves ribbon_trim sextuplets smile split_head unzipping white_hoodie yellow_hoodie yellow_liquid
33140410 ahoge akumatsu black_hair blue_hoodie fingernails green_hoodie highres hood hoodie kamimatsu long_earlobes matsuno_choromatsu matsuno_ichimatsu matsuno_jyushimatsu matsuno_karamatsu matsuno_osomatsu matsuno_todomatsu osomatsu-san osomatsu_(series) pink_hoodie purple_hoodie red_hoodie ribbon-trimmed_sleeves ribbon_trim sextuplets smile split_head unzipping white_hoodie yellow_hoodie yellow_liquid
10s 1boy akumatsu black_hair capri_pants character_name closed_eyes colored_sclera denim multiple_expressions grey_background hood hoodie jeans male_focus messy_hair nose_picking osomatsu-san osomatsu_(series) pants pointy_ears red_sclera sharp_teeth simple_background smile solo sparkle teeth translation_request yellow_eyes yoshi_gumi
10s 1boy akumatsu black_hair capri_pants character_name closed_eyes colored_sclera denim multiple_expressions grey_background hood hoodie jeans male_focus messy_hair nose_picking osomatsu-san osomatsu_(series) pants pointy_ears red_sclera sharp_teeth simple_background smile solo sparkle teeth translation_request yellow_eyes yoshi_gumi
10s 2boys akumatsu angel_wings arrow_(projectile) backlighting belt black_hair blue_necktie cross demon_wings diamond_(shape) formal_clothes grin highres izumi_(milkywhite2) kamimatsu long_earlobes male_focus meme meme_attire messy_hair multicolored_background multiple_boys necktie osomatsu-san osomatsu_(series) ribbon shirt smile striped_clothes striped_shirt suit the_dress_(meme) wings yellow_necktie
10s 2boys akumatsu angel_wings arrow_(projectile) backlighting belt black_hair blue_necktie cross demon_wings diamond_(shape) formal_clothes grin highres izumi_(milkywhite2) kamimatsu long_earlobes male_focus meme meme_attire messy_hair multicolored_background multiple_boys necktie osomatsu-san osomatsu_(series) ribbon shirt smile striped_clothes striped_shirt suit the_dress_(meme) wings yellow_necktie
1boy akumatsu black_hair brown_background colored_sclera commentary_request denim fingernails grin hand_in_pocket hood hoodie jeans kanatsuki looking_at_viewer male_focus messy_hair orb osomatsu-san osomatsu_(series) pants pointy_ears red_sclera sharp_fingernails sharp_teeth simple_background smile solo teeth yellow_eyes
1boy akumatsu black_hair brown_background colored_sclera commentary_request denim fingernails grin hand_in_pocket hood hoodie jeans kanatsuki looking_at_viewer male_focus messy_hair orb osomatsu-san osomatsu_(series) pants pointy_ears red_sclera sharp_fingernails sharp_teeth simple_background smile solo teeth yellow_eyes
10s 1boy akumatsu black_hair colored_sclera english_text evil_grin evil_smile grin hand_in_pocket male_focus nyaph osomatsu-san osomatsu_(series) red_sclera sharp_teeth smile solo teeth
10s 1boy akumatsu black_hair colored_sclera english_text evil_grin evil_smile grin hand_in_pocket male_focus nyaph osomatsu-san osomatsu_(series) red_sclera sharp_teeth smile solo teeth
10s 2boys akumatsu artist_name atarime bad_id bad_twitter_id black_hair claws earlobes evil_grin evil_smile grey_background grin hands_in_pocket hands_in_pockets highres hood hoodie kamimatsu long_earlobes male_focus multiple_boys osomatsu-san osomatsu_(series) red_eyes simple_background smile standing yellow_eyes
10s 2boys akumatsu artist_name atarime bad_id bad_twitter_id black_hair claws earlobes evil_grin evil_smile grey_background grin hands_in_pocket hands_in_pockets highres hood hoodie kamimatsu long_earlobes male_focus multiple_boys osomatsu-san osomatsu_(series) red_eyes simple_background smile standing yellow_eyes
10s 1boy akumatsu black_hair colored_sclera denim fingernails grin hand_in_pocket hood hoodie jeans kanatsuki looking_at_viewer male_focus messy_hair orb osomatsu-san osomatsu_(series) pants pointy_ears red_sclera sharp_fingernails sharp_teeth simple_background smile solo tan_background teeth yellow_eyes
10s 1boy akumatsu black_hair colored_sclera denim fingernails grin hand_in_pocket hood hoodie jeans kanatsuki looking_at_viewer male_focus messy_hair orb osomatsu-san osomatsu_(series) pants pointy_ears red_sclera sharp_fingernails sharp_teeth simple_background smile solo tan_background teeth yellow_eyes
10s 2boys akumatsu arm_behind_head beckoning black_hair blush brown_hair closed_eyes dakimakura_(medium) earlobes full_body kamimatsu long_earlobes male_focus messy_hair multiple_boys on_bed osomatsu-san osomatsu_(series) pajamas pillow pointy_ears sharp_teeth smile teeth yoshi_gumi
10s 2boys akumatsu arm_behind_head beckoning black_hair blush brown_hair closed_eyes dakimakura_(medium) earlobes full_body kamimatsu long_earlobes male_focus messy_hair multiple_boys on_bed osomatsu-san osomatsu_(series) pajamas pillow pointy_ears sharp_teeth smile teeth yoshi_gumi
2boys akumatsu angry blank_eyes closed_eyes formal_clothes garara382 hood hoodie kamimatsu long_earlobes matsu_symbol multiple_boys multiple_views open_mouth osomatsu-san osomatsu_(series) single_tear smile suit
2boys akumatsu angry blank_eyes closed_eyes formal_clothes garara382 hood hoodie kamimatsu long_earlobes matsu_symbol multiple_boys multiple_views open_mouth osomatsu-san osomatsu_(series) single_tear smile suit
10s 1boy akumatsu bad_id bad_twitter_id blunt_bangs colored_sclera frown hood hoodie male_focus matsuno_ichimatsu matsuno_karamatsu osomatsu-kun osomatsu-san osomatsu_(series) red_sclera sharp_teeth simple_background sitting sleeves_rolled_up smile teeth white_background
10s 1boy akumatsu bad_id bad_twitter_id blunt_bangs colored_sclera frown hood hoodie male_focus matsuno_ichimatsu matsuno_karamatsu osomatsu-kun osomatsu-san osomatsu_(series) red_sclera sharp_teeth simple_background sitting sleeves_rolled_up smile teeth white_background
10s 2boys akumatsu black_hair bookshelf character_name colored_sclera male_focus mask matsuno_karamatsu messy_hair multiple_boys nakamura_yuuichi osomatsu-kun osomatsu-san osomatsu_(series) playing_games red_sclera sharp_teeth sugita_tomokazu teeth tokyo_encounter voice_actor_connection
10s 2boys akumatsu black_hair bookshelf character_name colored_sclera male_focus mask matsuno_karamatsu messy_hair multiple_boys nakamura_yuuichi osomatsu-kun osomatsu-san osomatsu_(series) playing_games red_sclera sharp_teeth sugita_tomokazu teeth tokyo_encounter voice_actor_connection
10s 2boys akumatsu black_hair colored_sclera colored_skin earlobes hood hoodie hug kamimatsu long_earlobes male_focus multiple_boys osomatsu-san osomatsu_(series) red_sclera red_skin rey0 sharp_teeth tears teeth translation_request yellow_eyes
10s 2boys akumatsu black_hair colored_sclera colored_skin earlobes hood hoodie hug kamimatsu long_earlobes male_focus multiple_boys osomatsu-san osomatsu_(series) red_sclera red_skin rey0 sharp_teeth tears teeth translation_request yellow_eyes
10s 2boys akumatsu black_hair card colored_sclera comic earlobes hood hoodie kamimatsu long_earlobes male_focus monochrome multiple_boys osomatsu-kun osomatsu-san osomatsu_(series) playing_card red_sclera rey0 sharp_teeth spot_color teeth translation_request yellow_eyes
10s 2boys akumatsu black_hair card colored_sclera comic earlobes hood hoodie kamimatsu long_earlobes male_focus monochrome multiple_boys osomatsu-kun osomatsu-san osomatsu_(series) playing_card red_sclera rey0 sharp_teeth spot_color teeth translation_request yellow_eyes
akumatsu black_hoodie blood blood_from_mouth character_name colored_sclera fire garara382 hood hoodie humanization hunched_over looking_at_viewer looking_back messy_hair mixed-language_text multilingual_text osomatsu-san osomatsu_(series) red_sclera turning_head white_background
akumatsu black_hoodie blood blood_from_mouth character_name colored_sclera fire garara382 hood hoodie humanization hunched_over looking_at_viewer looking_back messy_hair mixed-language_text multilingual_text osomatsu-san osomatsu_(series) red_sclera turning_head white_background