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In other words, if I have a list with entries formatted "[Artist Name] - [Track Name]" without advanced knowledge of their corresponding YouTube URLs (if any exist), how might I script things so that YouTube searches for each entry, and generates the URLs for the first n number of identical or similar entries per a YouTube query?

Do any simple solutions come to mind that might lever wget, PowerShell, or Python?

3

roll.io seems to do exactly what you want, except for the download queue.

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