As the 1960s progressed, he also played at Minton’s (the iconic Harlem lounge where bebop gestated) and at the Playboy Club, where he met and became friends with Quincy Jones. In this same decade he played on Quincy Jones’ "For Love Of Ivy" film score (1968).
During these years, he also met Ray Brown and Oscar Peterson, who later recommended Alexander to Hans Georg Brunner-Schwer, the proprietor of Germany’s MPS label, for which he made a dozen records between 1971 and 1985.
Minton's Playhouse where Monty played throughout 1966-68
Monty and his family moved to Miami, Florida, in 1961, where he played in various nightclubs and would sublimate Jamaican roots towards establishing a jazz identity. Some of the very early places he remembers playing are: the Airliner Motel, the Bonfire Restaurant, Bunch Park Bowling Alley in Opalaca, the Windsor hotel with bandlear Art Mooney, and playing with bandleader Cliston Major better known as... C Major.
In early 1962 Monty was playing at Le Bi', a Miami Beach nightclub, when Sinatra stopped by with his good friend Ermenigildo "Jilly" Rizzo. Rizzo owned his own club—Jilly's at 256 W. 52nd Street in NYC—that was Sinatra's primary hangout in Manhattan. Sinatra and friends were impressed and there was talk of Monty going to New York to play at Jilly's but nothing came off of that first interlude.
Six months later in Reno, Nevada, lighting struck twice as the same chance encounter with Jillly and Frank Sinatra took place when Monty was playing at the Thunderbird Hotel but this time, just a few days later, Rizzo bought Monty an airline ticket and the next night he was a regular piano player at Jilly's, playing for a who's who of entertainers and musicians. At Jilly's he met Miles Davis and Count Basie and he quickly became a fixture in the New York scene, also playing frequently at the newly opened Playboy Club.
At Jilly’s, for the next four years, Monty’s trio with a rotating stellar cast of bassist and drummers (Ron Carter, Roy Haynes, Tony Williams, Al Harewood, Bob Cranshaw, Mickey Rocker, Sonny Payne, Tommy Williams, George Tucker) swung until the wee hours of the morning for Sinatra, a mix of celebrity entertainers, tough guys, thrill seekers, and such iconic jazzfolk as Miles Davis, Count Basie, and Milt Jackson.
In Los Angeles, in 1964, Alexander recorded his first album, Alexander the Great, for Pacific Jazz at the age of 20. The album was very energetic and upbeat with the climax tune being "Blues for Jilly".
What was it like to play at the popular celebrity hangout, Jilly’s Saloon? What are some of your favorite memories from those day?
MONTY: "So many that revolve around Sinatra because he was such…you may say the king of show business. He would come to Jilly’s because Jilly Rizzo was his best friend. They were like brothers. Jilly and Sinatra heard me playing in a Miami beach club and hired me on the spot. So I took the job.
It was small place, about 60 people, and all the celebs of the time went there. Among them were movie stars. I remember Judy Garland was a frequent visitor. People in Sinatra’s circle, Peter Lawford and Sammy Davis. Frank Sinatra loved the jazz artists. He and Count Basie would sit together and have drinks till 5 in the morning, and I’m playing the piano in the corner. Miles Davis started coming in regularly. He would sit at the piano bar and one night he came over to me, and he wrote his phone number down, and he said I want you to come by the house so I started hanging out with Miles Davis. And that’s a fact. I remember one night playing and next to me was Miles Davis and Frank Sinatra in deep conversation. I’ll never forget that moment when these two icons of music were hanging out there together."
(From the Interview with Jade Shojaee, DRRA)
Tony Bennett and Damita Jo swing to the beat of Kai Winding Quintet, with Monty Alexander at piano, during "jazz 'n' Cocktails" at the New York Playboy Club.
Monty Alexander in person with Jazz Times on NYC,
Jilly's and Frank Sinatra
Frank Sinatra's quote in the back of Monty's first album:
"The kid is a gas".
This is a detail of that back cover, which also include a quote from Quincy Jones whom Monty first met at the Playboy club when Q. was the A&R man at Mercury records. Shortly after Quincy moved to LA where he started his successful film scoring career.
MONTY: “It was a most memorable time and I have such fond memories of being at Jilly’s.
I was nervous, but I had a great bass player, Bob Cranshaw. I don’t read music so I have to use my ears. I knew the songs of Sinatra such as "I’ve Got You Under My Skin" and "I Get a Kick Out of You", but Bob was leaning over and saying: ‘G, D, B flat’, and I pulled it off because I’m instinctive. All I know is Sinatra turned around with a big smile. That was it. He was one of those people who inspire you, he would come over and say things like: ‘Keep swinging kid’ or ‘You’re swinging’ or ‘ You’re grooving’.
I met Miles Davis at Jilly’s. Miles dug my playing and he had me come over to his place and hang out. It taught me confidence because half of the stuff is being confident so that when you play ‘that’ note on the piano or trumpet, it’s the right note, not another note, but ‘that’ note, which comes only from a sense of security, and it really helps when your heroes tell you to ‘keep going’."
What was it like playing at Jilly’s?
"Well, I thought life would end, because it couldn’t get better than this. I was 17, I realized I was in very fast company. Not just in jazz, but in all the top entertainers in show business. Judy Garland is sitting at the piano bar. I look around and Sammy Davis is walking in. I played at private events at Frank Sinatra's apartment. He was a good friend. That crowd, they wanted to hang out until 6 a.m. I would keep it going until then. Miles Davis would come in. Count Basie was sitting there with Frank. That's where I met Milt Jackson. I was learning so much at this time."
(Don Albert, IOL, South Africa interview)
This was the front entrance of the New York Playboy Club at 59th street between Fifth and Madison avenue...
This is some of what you might have heard if you had been hanging out at Jilly's or the Playboy club in the '60s...
"Girl Talk" was recorded in 1967 with Bob Cranshaw on bass and Al Foster on drums. Bob Cranshaw and Al Foster were frequently hired by the 23 year old Monty to play in both venues in those years...
Spunky was recorded in 1964 and features Victor Gaskin on bass and Paul Humphries on drums.
This is a 1965 photo of the Detroit Drome Lounge (photo credit: Leni Sinclair).
Look carefully and you will see Monty's name is listed as the coming attraction being advertised below Yusef Lateef on the billboard.
Monty and Paul West on bass at Baker's Keyboard Lounge in Detroit.
--Jimmy Cobb was on drums that night; his snare drum appears at the bottom and center. (1967)
Monty at the legendary Baker's Keyboard Lounge.
The table tent schedule on the right lists their 1967 line up with his appearance alongside that of true original Jazz masters.
This Milt Jackson Quintet album, titled "That's the Way it is" (Impulse), was recorded live at famed LA Jazz club Shelly's Manne-Hole in 1969 and features Monty on the piano--his first gig and first recording with Jazz giants Ray Brown and Milt Jackson.
Here's the first track... Monty playing the bass line on the piano while Ray Brown solos.... hot stuff!!!
Eddie Fisher manages
Le Bi ad Monte (Monty) Alexander
1963, 21 January
(this ad of Monty appearing at the Bistro in Miami is just about the first time he met Jilly's and Frank Sinatra...)
23 May, 1962
16 Aug. 1963, Reno Gazette Journal
Radio Interview - NPR
Monty Alexander: "Living the Good Life"