[1] The album consists of covers of traditional pop standards made famous by Frank Sinatra, chosen by Dylan.

[6] Most of the songs are Tin Pan Alley standards, delivered in a slow to mid-tempo pace, that "often luxuriate in melancholy" and communicate a sense of loneliness.

[6] The arrangements center on Dylan's vocals supported throughout by Donny Herron's gliding pedal-steel guitar and Tony Garnier's bass.

[6] The back cover photo shows Dylan and a masked woman, both in formal wear, sitting at a small nightclub table looking at a seven-inch Sun Records single.

[9] The album was officially announced on December 9, 2014,[10] and two singles, "Full Moon and Empty Arms" and "Stay with Me", were released the following month.

[11] Just prior to the album's release, a Dylan publicist announced that 50,000 free copies of the CD would be given away to randomly selected readers of AARP The Magazine, a bi-monthly periodical that focuses on issues related to aging.

The video, which starred Dylan and actor Robert Davi, was shot in high-contrast black and white and featured a crime plot meant to evoke classic Hollywood film noirs of the 1940s and 1950s.

His vocal abilities proved incorrect those terrible, 50-year-old jokes about Dylan not being able to carry a tune — Bob can sing when he wants to".

[18] Kenneth Partridge, in Billboard magazine, gave the album four out of five stars, noting that Dylan was "singing like a guy who has seen it all and found truth in timeless poetry that belongs to everyone".

[29] Partridge also observed, "Dylan has always loved American mythology and all things archaic, and his best songs on recent albums have been rooted in pre-rock pop.

When he gets wistful on "The Night We Called It a Day" or grabs hold of moonbeams on the South Pacific favorite "Some Enchanted Evening", he's natural and sincere".

[22] Jesse Cataldo of Slant Magazine thought that the album "deepens the innate sorrow of these old tunes by establishing them on a long, irregular continuum, possessing the same inherent mutability as the folk songs of Dylan's early days".

Club, Corbin Reiff summed up the unexpected album by writing, "You can chalk it up as another instance of one of the most capricious artists in pop music history doing what he felt like.

[19] Paste magazine critic Douglas Heselgrave stated that "Every performance on Shadows in the Night expresses a level of vocal maturity and intuition that he's never quite reached before".

[31] David Fricke of Rolling Stone magazine described the album as "quietly provocative and compelling", observing that "Dylan transforms everything on Shadows in the Night into a barely-there noir of bowed bass and throaty shivers of electric guitar".

Pareles further stated: "Even when it falters, Shadows in the Night maintains its singular mood: lovesick, haunted, suspended between an inconsolable present and all the regrets of the past".

[6] In his review for The Daily Telegraph, Neil McCormick described the work as "quite gorgeous" and "spooky, bittersweet, mesmerisingly moving" with "the best singing from Dylan in 25 years".

[20] McCormick also praised Dylan's "delicate, tender and precise" singing that somehow "focuses the songs, compelling listeners to address their interior world in a way glissando prettiness might disguise".

He later complained that the singer's voice sounds "permanently shot" and that "the Sinatra-style pop canon Dylan has devoted himself to lately does generally require some show of mellifluousness and pitch control".

[32] NJArts critic Jay Lustig admitted that while he didn't understand why Dylan recorded Shadows in the Night, he did "like his tender, sensitively phrased version of Cy Coleman and Joseph McCarthy’s “Why Try to Change Me Now", which he cited as his favorite track on the album.

Starr claims that the 73-year-old Dylan's vocal performance on "That Lucky Old Sun" is "analogous" to the way that the 64-year-old Sinatra "becomes audibly more energized and 'younger'" as the "Theme from New York, New York" progresses: "Dylan smooths out his voice, relishing and prolonging all the long, open vowels every time he sings 'roll around heaven all day', as if he is transfigured by the vision.

[38] Critic Ray Padgett also considers "That Lucky Old Sun" to be the highlight of Shadows in the Night (as well as the best of all 52 of the songs that appear on Dylan's American Songbook albums).