4 Songs That Make the Case for ‘Tell Tale Signs’ As the Best of the Bob Dylan Bootleg Series

Bob Dylan keeps churning out different versions of his Bootleg Series to give his fans a thorough overview of everything he’s recorded. Some of these collections have been more revelatory than others. Tell Tale Signs, released in 2008, stands as one of the best of the Bootleg Series releases.

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The double album collected material from 1989 to 2006, a period that included Dylan’s slow retreat from recording original material and his stunning comeback. These four songs, to that point either unheard or somewhat obscure, highlight the set.

“Red River Shore”

When Bob Dylan came rocketing back with Time Out Of Mind in 1997, many fans expressed shock at his comeback from an artistic slump. Little did they know that he left a song on the cutting-room floor that easily could have competed for best track on the album. “Red River Shore” partially borrows its title from the Carter Family classic “The Girl On The Greenbriar Shore”. In Dylan’s song, the narrator wends his way wearily through his life, unable to shake the memories of the titular character. Had the song just stayed in that lane, it still would have been brilliant. But in the closing moments, Dylan delivers some lines that make us question everything we’ve heard, somehow making the song darker and more devastating in the process.

“Tell Ol’ Bill”

Dylan focused on soundtrack work for a stretch at the turn of the millennium. The most famous of these songs, “Things Have Changed”, landed him an Academy Award. But the other three songs, all of which appear on this list, deserve more attention. Part of the reason they were obscure is that the films they adorned didn’t do a lot of business. In the case of “Tell Ol’ Bill”, it first appeared on the soundtrack to a drama called North Country, which starred Charlize Theron. From what we can tell, the song itself has little to do with that movie’s plot. But it does find Dylan singing some cutting one-liners over a jaunty rhythm. The version on Tell Tale Signs adds a bit of dusky atmosphere to the proceedings.

“Huck’s Tune”

Unlike “Tell Ol’ Bill”, “Huck’s Tune” at least seems to bear some resemblance to the movie in which it appeared. That would be Lucky You, which dealt with a professional poker player. Dylan has a lot of fun with the gambling references. “You put it all in and you’ve no chance to the win,” he sings at one point. And then later, he claims, “I’m stacked high to the roof,” likely referencing a pile of chips on the table. But for most of the song, he deviates from that topic to tell the story of a relationship that has served its purpose but now must be set aside. “I’m gonna have to put you down for a while,” he moans. His voice betrays the fact that this necessary move will bring him no happiness.

“‘Cross The Green Mountain”

Dylan has written his share of excellent anti-war songs in his time. Many of them came in his earliest years of recording, as he was shaken by the potential of nuclear war. In the case of “’Cross The Green Mountain”, he went all the way back to the Civil War. The song was earmarked for Gods And Generals, a 2003 film about that 19th-century conflict. Dylan’s sharp instrumentalists deliver a slow martial beat and a sad fiddle that sound as if they could have been played by some ragtag band to cheer up the troops. Dylan’s narrator frames his tale as “a monstrous dream.” But as the song progresses and the atrocities pile up, we know that the narrator was just using the dream as a defense mechanism against horrifying reality.

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