In the mid-1960s, Frank Sinatra's recording career had begun to falter. It was the age of Beatlemania, and the crooner's sound, rooted in jazz and big band music, was no longer in vogue.

Eager for another shot at topping the pop charts, Sinatra lined up a session in the spring of 1966 with Jimmy Bowen, a staff producer for the singer's label, Reprise, who had a knack for producing hit singles. Even though he despised the song, Sinatra took Bowen's advice and cut “Strangers in the Night.”

Bowen knew what he was doing. Released just over 50 years ago, in April 1966, “Strangers” shot up the charts, eventually knocking The Beatles' “Paperback Writer” out of the No. 1 spot and giving Sinatra his first chart-topper in a decade. Sinatra would quickly follow up “Strangers” with an album of the same name. It, too, became a smash. Ol' Blue Eyes was back.

Sinatra fans, appropriately, credited the Chairman of the Board for the success of the Strangers in the Night album. Some smaller, savvier number praised its contributing musicians, songwriters and producer Sonny Burke, the individual who oversaw its studio production. Undoubtedly, few celebrated the album's recording engineer, the skilled studio technician charged with capturing, whether through skillful mixing, clever editing or a combination of both, that mythical “perfect take.”

The engineer responsible for the masterful sound of Strangers was Lee Herschberg. While working at Hollywood's United-Western Recorders, Herschberg would man the board for some of the singer's biggest hits of the '60s, including the timeless “Summer Wind” and the career-defining “My Way.” Soon after, he became chief engineer for Warner Bros. Records, where he remained for several decades, working on records by James Taylor, Paul Simon, George Harrison, Eric Clapton and Rickie Lee Jones, among many others.

Reached by telephone at his Camarillo home, the 85-year-old Herschberg exudes humility, suggesting that his success, particularly with Sinatra, stemmed mostly from being at the right place at the right time. “Those were wonderful years,” he says. “I was really lucky to be around at the time. Timing is everything in life, I think, and mine was pretty good as far as a career goes.”

But luck had little to do with the magic behind the Herschberg-Sinatra partnership. “Sinatra was a perfectionist,” says Steve Hoffman, an acclaimed mastering engineer who has remastered Sinatra albums from the Herschberg era. “He always recorded live, and during the mid-'60s, even an up-to-date studio like United-Western only had three or four [recording] channels to utilize. So Lee had to 'premix' the session on the spot, with Sinatra singing with an orchestra and expecting everything to be done correctly, the first time, with no retakes.”

A bit of studio trickery often was involved as well. “As Sinatra aged and his voice started showing a bit of strain, Lee started editing together certain takes to make a seamless master take,” Hoffman explains. “Lee did this without the edits being audible. Lee's a master engineer, one of the few who could work with an imposing figure like Sinatra and coax out a performance that would be remembered years later.”

A child of the Depression, Herschberg developed a love for jazz and big band music while growing up in Chicago. He served as an instrument flight instructor in the Air Force during the Korean War, then settled in Los Angeles in the early '50s.

After a referral from a family friend, the bearded, dark-haired Herschberg took a job in Hollywood with Decca Studios in 1956, seeing it as a chance to combine his fondness for music with his aptitude for electronics. He apprenticed, learning the basics of recording from the head engineers while working sessions for Liberace, Bing Crosby, Ella Fitzgerald and Louis Armstrong. During these years, he also worked closely with Decca A&R man and arranger Sonny Burke.

In 1962, a corporate takeover of Decca by MCA suddenly put Herschberg and the rest of the Decca Studio staff out of work. But many former Decca employees, including Burke and Herschberg, would land on their feet at United-Western. There, Sinatra recruited Burke to produce albums for his new label, Reprise Records — and Burke would enlist Herschberg to help engineer them.

Eager to capitalize on the success of his “Strangers” single, Sinatra summoned Burke and Herschberg into United-Western in May 1966 to cut tracks for the forthcoming Strangers in the Night. After years of serving largely as an assistant, this would be Herschberg's chance to truly step to the fore as an engineer.

By now, Herschberg knew Sinatra's prerecording routine. “I had an office in Western, which was adjacent to the studio,” he explains. “It had a piano in it. Sinatra was supposed to go in there an hour early with his piano player, Bill Miller, and go over the arrangements.” In the meantime, Herschberg and Burke would be in the control room, adjusting levels on the studio microphones and balancing the control room's monitors while the orchestra ran through the session's compositions.

“Lee's a master engineer

But not infrequently, the impeccably dressed Sinatra would walk into the studio some minutes ahead of schedule, raring to go. “Sinatra loved the live orchestra, and was the biggest fan of the musicians,” Herschberg says. “It was like a family reunion when he would get into the studio. He knew all of the guys, and they all loved working with him. He'd hear them playing, and he'd say, 'That sounds great! Let's record this!' So a lot of times I didn't even have time to run down the orchestra, start listening to mics and sections of the band to get a balance on anything. You had to be really on your toes, all the time.”

Even though Sinatra's eagerness to record raised the degree of difficulty for Herschberg, he lived for these moments. “To me, being in the studio and having a huge orchestra and getting it all together and making it sound like it's supposed to sound and doing two or three songs in three hours, that was a great high for me. It required total concentration.”

Sinatra, too, was in his element, and most typically in a jovial mood. Herschberg says, “He was at his friendliest and nicest when he was in the studio. Sinatra loved to work standing out next to the rhythm section, right next to the conductor, with the orchestra spread around him, with the brass on one side, the saxes on the other, and the strings in the back. So there was no going into a vocal booth or anything like that. Never. He'd stand there and sing.”

While in later decades artists often spent weeks or months working in the studio, the American Federation of Musicians rules for session musicians, along with Sinatra's own interest in getting things recorded quickly, left Herschberg with no such luxuries. “You could only record up to 15 minutes of music in those three hours,” Herschberg recalls. “If you ran over, say, 30 seconds, the union would charge everybody another half session, I believe. So it was a rush to get everything done in three hours.” This meant that all the songs for Strangers in the Night, except the already released title track, had to be cut in a pair of breakneck, three-hour sessions.

To get a balanced sound on tape, Herschberg started with Sinatra. “I always tried to mix around his voice,” he explains, “so we'd have something that would fit the track. You didn't have to do a lot to it. All you had to do was leave him enough room for his dynamics. That was pretty much it. You could make adjustments afterwards.”

Herschberg understood that, like the other musicians in the room, Sinatra was playing an instrument: his microphone. “He was great on the microphone. He probably worked a microphone better than anybody I've ever seen in my life. He never missed a syllable.”

The results of those two May sessions, as documented on the Strangers LP, are sonically stunning. Sinatra sounds ebullient within the sparkling Herschberg mixes, his rich baritone alternately gliding and booming over Nelson Riddle's now-iconic arrangements. The instrumentation, too, presents an updated Sinatra sound. Riddle, wanting things to really swing, featured a Hammond B3 rather a piano. Along with the organ, the drums occupy a relatively prominent place in the mix, giving the album a touch of a rock feel in places.

Upon its release in June, the album performed like the “Strangers” single, galloping up the charts over the course of the summer, on its way to platinum sales. Frank Sinatra had come back in a big way.

The album was likewise a career maker for Herschberg. For his marvelous technical work on Strangers, Herschberg, along with Eddie Brackett, who'd engineered the title track, would win a Grammy for the Best Engineered Recording for the year 1966. “That was my one and only,” he says with a smile. “People ask me, 'Did you ever win a Grammy?' A lot of people who ask weren't even born in 1966!”

As the '60s drew to a close, Sinatra showed little signs of slowing down as a recording artist, and remained as eager as ever to work in the studio. Herschberg, who worked dozens of his sessions, came to the studio focused, ready to roll tape at a moment's notice.

Still, for 1969's My Way, Herschberg confesses that he nearly missed getting the take of the title track, perhaps Sinatra's best-known song, recorded during a December 1968 session at Western.

“It's a long song. I only heard about a minute and a half of the arrangement being run down” before Sinatra walked to the microphone, Herschberg recalls. With producer Sonny Burke at his side, the engineer quickly rolled tape.

As the song built to its magnificent crescendo, he noticed something amiss. “About halfway through, I looked over at the tape machine, and the meters were kind of pinned.” The recording levels on Sinatra's microphone were set too high, distorting the singer's voice. “I thought, oh my God. My second engineer had made a little mistake in setting up the tape machine.”

When he mixed the song, however, the ever-resourceful Herschberg found a fix. “His voice did have a little bit of an edge on it in spots, but in the mix, with the orchestra, you never heard it. It was a very dynamic arrangement. It went from very soft to huge-sounding at the end.”

For Herschberg, the experience was just another reminder of how Sinatra liked to work. “It was done in one take, but that wasn't unusual at all for Sinatra. You had to be prepared to go from note one when he walked in.”

[Correction: An earlier version of this article incorrectly listed Lee Herschberg's age is 86. His actual age is 85. We regret the error.]

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