I don't know about the toughest, but Led Zeppelin's songs have got be among the most difficult ones. Communication Breakdown, Whole Lotta Love, Stairway to Heaven (the high part at the end), Black Dog, Rock n' Roll and so many others. Also, some Journey songs, such as Mother Father and Don't Stop Believin', are really difficult as well. Myles Kennedy's stuff is also really difficult to sing.
For me it's Blow your Speakers by Manowar, though I haven't seen any evidence of Eric singing it live anywhere near as good as he does on the studio album.
"Birth Ritual" by Soundgarden used to be my 'show off' song and taught me a lot about vowel modification and use of consonants. Nowadays though, it's outwith my range so it's something I'm trying to work back to but with proper technique.
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