Dylan’s 22nd studio LP came at a curious time. After a trilogy of odes to his relatively brief conversion to Christianity, he returned to a mostly secular style (to the relief of countless fans who felt confused by that strange but intermittently interesting detour). After Elvis Costello, David Bowie, and Frank Zappa politely declined to produce this quasi-comeback album (mostly due to scheduling conflicts), Dylan recruited Dire Straits leader Mark Knopfler for the job. Both Knopfler and former Rolling Stone Mick Taylor provide exemplary guitar work, and hiring the famed reggae rhythm section of Sly Dunbar and Robbie Shakespeare is an inspired choice.
The music has a slick if slightly dated feel to it—this was the ‘80s, after all—but the band is in the pocket, and they serve the compositions beautifully. The smooth reggae of opener “Jokerman” brings a shimmering quality to perhaps one of Dylan’s best 1980s songs. Despite occasionally venturing into odd bits of political conservatism on rollicking numbers like “Neighborhood Bully” and “Union Sundown”, he also brings along plenty of warm romance thanks to gorgeous ballads like “Sweetheart Like You” and “Don’t Fall Apart on Me Tonight”. While most people seem to love Infidels, not enough are quick to bring it up as a favorite. – Chris Ingalls
Empire Burlesque (1985)
If you want to sample prime 1980s Dylan, Empire Burlesque is your best bet. It arrived almost exactly in the center of the decade (June 10th, 1985), just a month before Dylan confused a huge global audience with a shambolic performance with Keith Richards and Ron Wood at the quintessential ‘80s event: Live Aid. Introduced by Jack Nicholson as “the transcendent Bob Dylan”, he and his Stonesy pals strummed their way through three of his early classics. Dylan also made an offhanded comment that led to the creation of the Farm Aid concert/organization by Willie Nelson, John Mellencamp, and Neil Young.
Empire Burlesque Bob is the exact opposite of the Live Aid Bob, as Dylan navigates the shiny trappings of ‘80s production (particularly on the synth-and-horn-drenched “When the Night Comes Falling from the Sky”). The production is a bit more dated than on Infidels, but if you can deal with it, you’ll be treated to a decent set of Dylan songs that range from pop (“Tight Connection to My Heart”) and rock (“Clean Cut Kid” and “Trust Yourself”) to pure balladry (“Never Gonna Be the Same Again”). In addition, the O’Jays would transform “Emotionally Yours” into a classic soul tune six years later. – Rich Wilhelm
World Gone Wrong (1993)
When you look at his discography, it’s easy to see that the late ‘80s to early ‘90s was a frenzied time for Dylan. He was busy releasing a series of decidedly un-stellar studio albums (Knocked Out Loaded, Down in the Groove, and Under the Red Sky), plus a poorly regarded live album with the Grateful Dead. In the midst of it all, though, 1989’s Daniel Lanois-produced Oh Mercy was critically acclaimed as one of Dylan’s many returns to form. Throw two Traveling Wilburys albums into this mix, and it would have been understandable if Dylan was feeling burnt out by the dawn of the decade. Instead, he recorded two acoustic albums: Good as I Been to You (1992) and World Gone Wrong (1993).
Both are worth seeking out, but the second one certainly gets the edge. His singing is warm and casual, and his song selection of bluesy folk/folksy blues tunes is predictably impeccable. However, what might be most surprising about World Gone Wrong is Dylan’s lively guitar playing, particularly on Blind Willie McTell’s “Broke Down Engine”. The record happened at the height of grunge, too, so it was generally ignored; nevertheless, it was the right move for Dylan at the time, setting the table for his 1997 masterpiece, Time Out of Mind, and all that came after it. – Rich Wilhelm
Together Through Life (2009)
Together Through Life, which caught fans by surprise in the spring of 2009, is not one of Dylan’s heavy-duty albums. Case in point: its closing track, “It’s All Good”, a sardonic meditation on the titular phrase that was all the rage at the time. Elsewhere, Dylan notes that hell is his wife’s hometown in a tune so thoroughly immersed in Chicago blues that he shared its songwriting credit with Willie Dixon. Another tune is named “Jolene”, and I hope to God that it’s an alternative view of Dolly Parton’s “Jolene” (but there is really no way to know). While the album is steeped in blues guitar, David Hildalgo of Los Lobos and his accordion bring a subtle Tex-Mex vibe to the proceedings. Together Through Life might not be Dylan’s best album by a long shot, but it sure is fun. Speaking of fun, 2009 was also the year Dylan graced us with Christmas in the Heart, a straightforward yet wildly enigmatic Christmas collection that I will be enjoying and defending for the rest of my life. – Rich Wilhelm
Shadows in the Night (2015)
While Dylan’s occasional retrenchments have often been retreats into acoustic music, per World Gone Wrong, 2015’s Shadows in the Night found Dylan seeking inspiration in songs associated with Frank Sinatra. While some of these picks are well remembered today (namely, “Autumn Leaves” and “Some Enchanted Evening”), others—such as album opener “I’m a Fool to Want You”—are less obvious. The sparse musical settings suggest that Dylan has stumbled into a roadhouse in the middle of nowhere and decided to sit in with a sleepy band that was just about to call it a night before he showed up.
We all know that Dylan’s voice isn’t for everybody and never has been, but Shadows in the Night is a late period vocal tour de force that finds him carefully working his way through each of its tunes. The desolation reflected in the music might be a bit much for daytime listening, but maybe that’s why he titled the album Shadows in the Night in the first place. Dylan continued down the Sinatra path with 2016’s Fallen Angels and 2017’s Triplicate, yet you may just find that Shadows in the Night is enough to satisfy whatever Sinatra/Dylan fixation you have. – Rich Wilhelm