photo: John Cohen/Getty

The announcement of Bob Dylan’s 36th and latest studio album Shadows in the Night again raised eyebrows in confusion, or at least in curiosity, over the fact that it would contain no original material and only feature traditional pop standards recorded by Frank Sinatra. The obvious question was: “Why would a singer of Dylan’s limited means (a means that grows rougher as his Never Ending Tours take their inevitable toll) attempt a catalog of songs that previously relied on the singer being in fine form?”

The key might be that Bob’s new album opens with “I’m A Fool To Want You,” the song that also opened Billie Holiday’s Lady in Satin, itself a controversial album, due to Holiday’s declining vocal strength. For many, it remains a classic.

Bob’s career has been full of odd moves — unpredictable, most would say. Besides, his decision to often choose inferior takes or inferior songs on what could’ve been excellent albums, he’s also made some broader humdingers that have made us question the man’s sanity. Or at least made us wonder if he’s messing with us.

Let’s look at a few of Bob’s weirder career decisions!

9. Going Country in 1969

Most performers look for ways to increase their audience, to build “market share” by capitalizing on trends and/or playing to their strengths. First, Bob had a “motorcycle accident” that canceled his future concerts in 1966. Then, he released the understated John Wesley Harding album that was very much the antithesis of the psychedelic times of 1967 and when that didn’t thoroughly alienate his audience, he issued Nashville Skyline, which resulted in one of his biggest hits, “Lay Lady Lay” and such un-Dylan-like fare as “Nashville Skyline Rag,” “Peggy Day,” and “Country Pie.” When that didn’t completely lose his audience, he made…

8. A Deliberately Bad Album

Deliberately bad? It sure seemed like it. Yep, a double album, ironically (?) titled Self Portrait, of lukewarm covers (Paul Simon’s “The Boxer” complete with Bob haphazardly harmonizing with himself), a lifeless remake of “Like a Rolling Stone,” and original songs with titles like “Woogie Boogie” and “Wigwam.” It seems impossible to figure Bob thought any of this was good. The album was considered so bad, it even angered Rolling Stone magazine with a review that asked “What is this s---?” Bob released a new album, New Morning, three months later to apologize for going too far.

7. Performing in Kiss Makeup!

Bob caked his face in white makeup, looking like he was awaiting orders from Gene Simmons himself as to which character he would be in Kiss. When Gene didn’t call, Bob left his face all-white and assembled his own Rolling Thunder Revue where he brought along 60 of his best buddies to keep him company while he yelled out his songs from the stage.

6. The Born-Again Years

As if punk, new wave, and disco didn’t make Bob seem old and behind-the-times, he decided to take matters into his own hands and harass audience members for not paying attention during Bible class. While transforming into a Bible-thumping preacher had its curious onlookers — and “Gotta Serve Somebody” tickled those who always think everything’s going to hell — overall, it guaranteed Dylan “grumpy old man” status for most of the ’80s.

5. Live Aid

Bob held senior status when it came to standing up for sociopolitical issues, despite not having written much protest material since 1965. Ignoring the grand theater of the video age, Bob hit the stage at Live Aid as the penultimate act with nothing more than his acoustic guitar and two drunk Rolling Stones who sounded like they knew “The Ballad of Hollis Brown” about as well as the audience.

photo: Richard E. Aaron/Redferns

4. Back-to-Back Acoustic Folk Albums in the ’90s

Nirvana altered the radio/MTV landscape for the first half of the 1990s, proving that loud but tuneful hard rock that wasn’t hair metal could succeed commercially. While Kurt Cobain wailed on Leadbelly, Bob Dylan put together 1992’s Good As I Been to You and 1993’s World Gone Wrong. The albums reflected Dylan’s roots and scored positive reviews. However, the lack of original material convinced people the great songwriter had dried up creatively and the cover of “Froggie Went A-Courtin’” failed to connect with Generation X.

3. Borrowing from the Works of Others

The only thing weirder than hearing that Bob Dylan has been allegedly lifting lyrics from a book called Confessions of a Yakuza and the Civil War poetry of good ol’ Henry Timrod is the idea that anyone else noticed. You mean there are two people still reading the poetry of Henry Timrod?

2. The 2004 Victoria’s Secret Commercial

People thought of Bob Dylan as the voice of the counterculture, never to be swayed by the evils of green paper. So, what was he doing in a TV ad for Victoria’s Secret? Was he endorsing the product because he loved it so? Did he owe someone a favor? Next up: Cadillac!

1. The Christmas Album

It sounded like an impossible rumor when word first leaked that Bob had recorded an album of Xmas merriment — Christmas in the Heart — that was based more on the crooning Bing Crosby era than the world Dylan helped transform. “I’ll Be Home for Christmas” sounded like an ominous threat. But it was just Bob throwing another curveball into the wind.