Songs That Surprisingly Match Shadow the Hedgehog!

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1. Evil Angel - Breaking Benjamin - Which mainly symbolizes Shadow's bond with Maria including their past together.

2. Point of No Return - STARSET - This would match well to how Shadow has chosen to let go of his past and continue to keep his promise to Maria.

3. Let You In - Ellen Rose - Now, I feel this would represent BOOM Shadow in a sense. He did claim in Rise of Lyric that he considers friendship as a weakness, so something must've happened in his unknown Origins that made him give into such belief that connects to this.
How do I see it as in his past? Betrayal.

4. Boulevard of Broken Dreams - Green Day - This would match a sense of path for Shadow. He may choose to go alone on such paths that may go for the better or worse, but it doesn't mean others will go for it. But later, Shadow does know that his teammates and companions, Rouge the Bat and E-123 Omega have his back no matter the odds. Despite how Mephiles the Dark tried to tear them apart in test to their loyalty, they stuck together like glue. This has proven to Shadow that while the world may be against him, he still has those who will care for him through the end.

5. On My Own - Ashes Remain - Shadow has went through a great influence of Post-Trumatic Stress Disorder when Maria was killed. After all he had done, and the fact he'll never see her again, he became an introvert and one who isn't willing to be involved with others so easily. It's quite understandable.
He soon got involved with Rouge the Bat and E-123 Omega, both are his partners in Team Dark, which he didn't seem to acknowledge much at first. But he had an instinct to look after them. He was willing to protect Rouge at his awakening right as Omega was as well and attacked, and listen to her when she got them to team up through the events of Sonic Heroes.
Even in Sonic 06, he has shown concern for the two in that time; he saved Rouge from falling, and saddens when he sees a destroyed Omega in the future,only to be even more hurt when he finds that the latter will seal him away.
In the end though, Shadow has come to see Team Dark as his family, and has looked after them as they did for him.
This proves that despite the odds and all tha is against him, Shadow is NEVER alone in the end.

(More will be ahead...)

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