Frank Sinatra’s Strangers in the Night won the 1966 Grammy for Record of the Year.  Never mind Dylan’s Blonde on Blonde, debuts by Love and Frank Zappa, the Beach Boys’ Pet Sounds, or the Beatles’ Revolver.  Clearly, changes were afoot in popular music and the Chairman of the Board was struggling to remain relevant (as the Grammy awards struggle to do nearly every year).  Despite the shifting cultural winds, the title track became the biggest hit of Sinatra’s long career.  Strangers in the Night: Deluxe Edition ultimately pales in comparison to later career highlights from the 1954-1961 period, but it still stands as one of Sinatra’s final victories against the rising youth movement.

The album strikes an uneasy balance between Sinatra fondly looking back to the past and reluctantly engaging the musical climate of the mid-1960s.  The album includes several songs from Sinatra’s youth: 1928’s “My Baby Cares for Me”, 1930’s “You’re Driving Me Crazy”, 1925’s “Yes Sir, That’s My Baby”, and 1935’s “The Most Beautiful Girl in the World”.  The singer sounds genuinely engaged in his performance of these songs from yesteryear.  All-star arranger Nelson Riddle infuses several of the more contemporary tracks with an affable organ bounce and lively horn charts in an attempt to meld with current sounds.  Despite Riddle’s best efforts, Sinatra’s performance on these tracks, “Call Me”, “Downtown”, and “On a Clear Day”, sound disinterested and comparatively uninspired.  On “Downtown”, in particular, Sinatra’s vocal embellishments at the end of phrases threaten to make a joke of the track.  It rapidly becomes apparent that Sinatra is not impressed with contemporary styles.  Petula Clark’s version of “Downtown” is rightfully more popular.

The title track and “Summer Wind” are easily the best tracks on Strangers in the Night: Deluxe Edition.  Sinatra’s voice is in fine form and the easy-listening majesty of these songs benefit from the digital remaster of the album.  Although the swelling orchestration of the karaoke staple “Strangers in the Night” does not fit with the rest of the album, its impact is undeniable.  “Summer Wind” is a better fit for the record, as it employs an appropriately winsome organ that underscores the nostalgic wistfulness of the track. 

In addition to the ten original tracks, this edition of the album includes three previously unreleased tracks: live versions of “All or Nothing at All” and “Strangers in the Night” from Budokan Hall in Tokyo during the 1980s, and an alternate take of “Yes Sir, That’s My Baby” from the original recording sessions.  The live tracks from the ‘80s are examples of Sinatra’s ‘80s singing style and a mildly interesting detour, but the alternate take of “Yes Sir, That’s My Baby” primarily sounds like the original version and therefore does not add much to the collection. 

Strangers in the Night: Deluxe Edition may not be the most essential Sinatra album to own, but “Strangers in the Night” still managed to bump the Beatles’ “Paperback Writer” from the number one spot on the pop chart in 1966.  For Sinatra himself, for the Sinatra fan, and as a pop culture moment in itself, that is certainly worth something.