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Kuroneko Chelsea · Naruto Shippuden · Naruto Shippuden ED 37
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shippai bakka shite make sou ni naru kedo
I do nothing but fail — I'm about to lose, but…
Failure only do, lose almost-become but — ばっか is the casual form of ばかり; 〜そうになる describes a state on the verge of happening.
Tone is very young-adult Japan: self-deprecating, self-affirming on the next breath. The casual ばっか is the kind of speech you'd use with close friends, not in a job interview.
warawareta tte ii yo kanarazu umaku iku sa
Even if I get laughed at, that's fine — it'll definitely work out, ya know.
Was-laughed-at even-if good (emphatic-yo), surely well goes (casual assertion-さ) — 上手くいく is a stock idiom for 'things go well, work out'.
上手くいく is the Japanese 'it'll work out / it'll go well'. Combined with 必ず it becomes a self-pep-talk: literal translation 'it WILL definitely go skillfully'.
gomen ne datte ienai
I can't even say 'I'm sorry'.
Sorry-(softening) even cannot-say — だって here marks 'even (a thing as small as) ごめんね'.
ごめんね with the soft ね is the gentle, affectionate way to apologize — to a friend or partner. Saying 'I can't even say ごめんね' is heavier than it sounds: it's confessing emotional paralysis.
akitai kurai ni kirai na tsuki no shita
Under a moon I hate so much I'd love to get sick of it — sick of it — sick of it.
Want-to-tire-of × 3, to-the-extent-of, hated moon's under — くらいに sets up a degree clause: 'to the point that…'.
Triple-repetition for emphasis: 飽きたい飽きたい飽きたい. 飽きる means 'tire of, get sick of' — 飽きたい (want to get sick of) is a strange wish: 'I wish I could even get bored with hating you, moon'. Pure post-breakup energy.
asufaruto no ue heddo-raito ga sabishisa terashitemo
On the asphalt — even if headlights illuminate (my) loneliness…
Asphalt's on, headlight (subj) loneliness even-if-illuminates — 寂しさ is a noun derived from 寂しい via the -さ suffix that turns adjectives into abstract nouns.
Cars passing on the asphalt at night, headlights revealing the protagonist's loneliness — quintessential Japanese-singer-songwriter imagery (think Yorushika, Tatsuya Kitani, KingGnu's quieter songs).
kuyokuyo suru na tte hoshi mo waratte iru yo
'Don't mope around' — even the stars are laughing (saying that).
Brood-do don't (quote), star also is-laughing (emphatic) — 〜るな is the abrupt negative imperative attached to dictionary form.
くよくよする ('to brood, mope') is itself half-mimetic — くよくよ evokes someone going in mental circles. The negative command 〜な is gruff but here used affectionately, like an older brother.
kesetara ii noni na nakitai kurai ni
I wish I could just erase it — I want to cry, want to cry, to the point that I want to cry…
If-could-erase good (regret) (self-directed), want-to-cry × 3, to-the-extent-of — 〜たらいいのに is the canonical 'I wish (but it isn't so)' pattern.
〜のにな at the end is the soft sigh of self-pity / regret. のに says 'though…' and the trailing な makes it a thought spoken to oneself: 'if only it could be… (sigh)'.
utaou utaou donna ni nakisou datte
Let's sing — let's sing — no matter how close to tears (we are).
Let-sing × 2, no-matter-how cry-looks-like even — 泣きそう combines the ます-stem of 泣く with 〜そう (looks like). どんなに〜だって = 'no matter how X'.
歌おう repeated twice + どんなに〜だって is the song's emotional pivot: even drowning in sadness, sing through it. Classic post-Naruto-shippuden ending vibe.