Sinatra: Top 10 Rock Swingers

On May 16, 1966, Frank Sinatra took his first stab at the modern rock idiom. Based on my research, the singer took the plunge with Downtown, the song that Petula Clark had made a hit a year earlier. Recorded by Sinatra at the tail end of the Strangers in the Night session, his reading was painfully stiff. Even with Clark perched on a stool at the date, Sinatra seems bewildered by the lyrics in some places, fed up in others. His recording of Winchester Cathedral in November for That's Life wasn't much better. The singer clearly didn't yet grasp how to adapt his ring- a-ding-ding thing to the gentle emotional feel of the emerging rock scene.

But Sinatra got hip in short order. Many of my favorite recordings of Sinatra's after 1966 are rock renditions. Personally, I was never big on Sinatra's coarse attempts to resurrect the glory of the 1940s and 1950s in the 1960s and 1970s. Too much was happening culturally for a look back at the American Songbook. Besides, many of his rehashes sounded stale and croaky compared to his original treatments. In addition, who needed yet another version of Street of Dreams or The House I Live In?

But the rock stuff--now that's a different story. Most of Sinatra's rock attempts still sound very cool. Once he figured out how to swing and connect with earnest simplicity, the rock songs he interpreted took on new life--and in some cases new meaning. Many of his versions came off like an aging bachelor who figures out how to do the frug and winds up displaying some pretty sharp moves. For me, the turning point was Ernie Freeman's arrangement for Don't Sleep in the Subway. By using a rock-swing chart with a female vocal chorus, Freeman [pictured] gave Sinatra a way to put his mid-life-crisis stamp on the genre.

Mind you, not all of Sinatra's rock attempts worked during this period. For example, Billy May's arrangement of Sunny and Don Costa's MacArthur Park were slowed to the point of non-recognition. But most of Sinatra's swinging rockers did work and continue to sound great.

Here are my 10 favorite uptempo Sinatra interpretations of rock-era hits, in chronological order:

Don't Sleep in the Subway (July 1967)--Originally a hit for Petula Clark in 1965, this track was recorded for Sinatra's The World We Knew. Ironically, the No. 1 pop-rock hit off the album wasn't this remake. It was Something Stupid--a tune written by C. Carson Parks that Sinatra recorded as a duet with his daughter Nancy.

Both Sides Now (November 1968)-- Recorded for Cycles, Sinatra delivers a compassionate feel on this mid-tempo hit written by Joni Mitchell, who recorded it as a single earlier in the year. What makes the Don Costa arrangement special is the harpsichord, which gives the Chairman a whiff of psychedelia.

For Once in My Life (December 1968)--This loping finger-snapper arranged by Don Costa was recorded for My Way. Written by Motown's Ron Miller and Orlando Murden for Stevie Wonder, who had a hit with the song earlier in the year, Sinatra's version probably could have been taken a shade faster. But it builds beautifully just the same. By the way, My Way was just remastered and reissued on CD as a 40th anniversary edition by Concord Records along with Frank Sinatra: Live at the Meadowlands.

Mrs. Robinson (December 1968)--Also recorded for My Way, this Paul Simon hit from the same year was given a wicked towel-snapping by Sinatra. Taken at the same tempo as Come Fly With Me, Sinatra treats this paean to older women with a semi-contemptuous, tongue-in-cheek rat pack feel. The result somehow manages to be both belittling and uplifting. Best of all, he tosses in odd ad lib lyrics throughout, including this blue bomb: “How's your bird Mrs. Robinson?" Hey, hey, hey. Makes you wonder what Paul Simon thought.

Tie a Yellow Ribbon Round the Ole Oak Tree (May 1974)--Tony Orlando and Dawn had a No.1 hit with this song by Irwin Levine and L. Russell Brown in 1973. Sinatra's version on Some Nice Things I've Missed swings and is much more rousing and playful.

Sweet Caroline (May 1974)--This Neil Diamond hit from 1969 also made it onto Sinatra's Some Nice Things I've Missed. The brassy, uptempo arrangement by Don Costa gives Sinatra a solid heavy bag to work out on, and the result amps up the original considerably.

You Are the Sunshine of My Life (October 1974)--Though Sinatra recorded this 1973 Stevie Wonder hit several times, the best version is the pulsating one recorded live for The Main Event. The version on Some Nice Things I've Missed is taken too fast while others are off for one reason or another.

Bad, Bad Leroy Brown (October 1974)--Sinatra recorded Jim Croce's blues hit live at Madison Square Garden for The Main Event. While the track reeks a bit from the same type of off-color humor Sinatra reserved for Sammy Davis Jr., he's more likely connecting with the song's flamboyant character as one egoist to another.

Oh Babe, What Would You Say (March 1975)--This one was a hit for Hurricane Smith, the pseudonym for Norman Smith [pictured], the engineer on many of the Beatles early albums up to 1965. Smith's wife Eileen wrote Oh Babe. Sinatra's version was never released commercially and was recorded during a failed session (none of the tracks recorded that day were released). But a close friend who's a Sinatra collector played a bootleg for me over the phone. Though Oh Babe is more of a rehearsal take than a master, the tune has a nice loose feel that still sounds better than Downtown.

Just the Way You Are (August 1979)--Sinatra recorded Billy Joel's 1977 hit on Trilogy. Though Joel's version remains definitive (and Barry White's is a close runner up), Sinatra's rendition hits a nice casual groove, and he retains the song's sincerity, which is more than we can say for his scorching of Mrs. Robinson.

Coming soon, my 10 favorite Sinatra rock ballads.