Bob Dylan’s Strangest Moments, From Lingerie to Sinatra

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Is Bob Dylan a weirdo?

An upcoming record of Frank Sinatra standards might seem particularly cuckoo for the rasping former voice of a generation, but Bob Dylan has spent most of his career throwing curveballs at fans.

That’s why his new record, “Shadows in the Night,” which comes out Tuesday, Feb. 3 (and is now attached to an AARP discount offer), might seem strange at first — until you realize all the other odd turns he’s made with his career, going back to ’65 when he infuriated his folkie fanbase by going electric.
Is Dylan an impish devil, genuinely curious and broad-minded, restless or a little lost or a bit of all of the above? Part of the fun and challenge of being a fan is trying to figure it out. One thing’s for sure, he doesn’t make it dull for his followers, so here’s a little look through Dylan’s back pages at some of his greatest goofs. Rest assured, there will be more to come from him …

“Christmas In the Heart” (2009) 

His holiday record wasn’t total crap, there were a few decent tunes there like “Must Be Santa” and “Christmas Island,” but otherwise, it could clear out many a room with ol’ Bobby trying to croak through yuletide classics.

The Victoria’s Secret’s ad (2004)

One of the biggest head-scratchers of his career came when not just one of his songs but Dylan himself appeared in a lingerie ad. In the video below, note what might have been the hilarious origin of this.

Notorious B.O.B. (1986, 2010)

Dylan the rapper made an appearance a few years back when footage surfaced of him doing a few lines from LL Cool J’s “Mama Said Knock You Out” on “Theme Time Radio Hour,” his now-defunct XM Satellite Radio show. But long before that, Dylan did cameo on a Kurtis Blow album in the mid ’80s.

Country Crooner (1969)

After his 1966 motorcycle accident and subsequent semi-retirement, Dylan came back as a Nashville Music Row songster and even brought Johnny Cash in for a duet on 1969’s “Nashville Skyline” album. Dylan probably did his best vocals here, for what it’s worth.

An Audience-of-One Concert (2014)

On Nov. 23 in Philadelphia, Dylan did one of his most memorable shows, but what was unique about it was who was in the audience: just one person. Fredrik Wikingsson was there for a Swedish film series called “Experiment Ensam (Experiment Alone)” and had the time of his life as you can hear from him here and in the video below.

Disco Dylan (1985)

OK, so it was the ’80s and even rock icons like Bruce Springsteen were putting synths in their songs, but it was kind of jarring to hear the loud drums, dance beats and electronic keyboards from Ol’ Bobby on “When The Night Comes Falling From the Sky.” The rest of the “Empire Burlesque” album wasn’t THAT bad, but it wasn’t one of his best either.

Sweet Jesus (late ’70s/early ’80s)

Robert Zimmerman had been kind of a lapsed Jewish boy for a while, though God would creep into his lyrics occasionally, but it was kind of a surprise in the late ’70s when he not only converted to Christianity but started to come out with religious-themed albums like “Slow Train Coming” and “Saved.” He even gave “sermons” to live crowds, who he’d usually never banter with otherwise before or after this time. Thank God he’d be back to being secular in the mid-’80s.

Crooked Reflection (1970)

In his self-exile, after going country, Dylan got sick of the bootleggers who were putting out his outtakes around 1969 (including the legendary “Great White Wonder”), so he decided to beat them at their own game with “Self Portrait,” which he felt was releasing his own outtakes on his own terms. It’s a fun, gutsy idea, but he had much better music in the vaults (like 1975’s “The Basement Tapes”), and the adult-pop production wasn’t well suited for him.

Slapstick Bobby (1990s)

“Seinfeld” writer Larry Charles revealed in a recent interview that sometime in the ’90s, Dylan got obsessed with Jerry Lewis and wanted to make and star in a slapstick comedy show for HBO, who green-lit the idea, but Bobby got cold feet soon after. The mind boggles at what that would have been like, but sadly, all we have is this November 2014 podcast interview with Charles telling the story about it.

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