On 2 March 1945, Phil married the former Miss America of 1942, the beautiful, Jo-Carroll Dennison. 
Just after Phil got hitched he accepted Frank Sinatra's request that he join him doing yeoman service on a U.S.O. tour of the Mediterranean area of Europe, leaving his wife, Jo-Carroll, home alone.
In post VE Day 1945, Phil performed for the US military, in Italy.  Accompanying him was old blue eyes himself, Frank Sinatra;  Betty Yeaton (billed as An Acrobatic Cutie);  and Fay McKenzie, who was a well known actress and singer.  The pianist and musical arranger was Saul Chaplin.

​The intrepid group played from camp to camp Rome, Casserta, Foggia, Pomigliano, Venice etc. Phil giving singing lessons, holding Franks mouth - squishing and pulling it in all kinds of shapes -  making constant fun of his leanness, tugging his ears and pinching his cheeks. No matter, whatever Frankie did, Phil would say it wasn't good enough. The audiences loved the routine, he was a classy brilliant act here.
  1. Lighter from Frank to Phil
    Lighter from Frank to Phil
The group continued tour of Europe, entertaining the troops, kept morale as high as possible amongst the GIs.​

When they arrived in Rome, they stayed at the luxurious Excelsior, the swankiest hotel in town. Frank Sinatra suggested they didn't waste their opportunity in this ancient city and that they should have an audience with the Pope.

"What've you been smoking?" asked Phil. Nevertheless Frank got in touch with President Roosevelt's envoy to the Vatican, Myron Taylor, and an appointment was made with his Holiness, at 3.30pm, via a certain door in the sacred building!!

One problem, what would the group wear for the visit? They really didn't have any formal neat and tidy clothes to don. Then they thought, oh yes!! our USO uniforms (which had yet to see the light of day). The girls proceeded to cover their heads by buying mantillas.

On the way, Phil immediately thought of his great friend Bing Crosby, the old groaner, who was a catholic, through and through and decided he'd get the Pope to bless some rosary beads for him.

The troupe were briefed on Vatican protocol by a Cardinal. He told them to kneel and to kiss the ring of Saint Peter. Then he glanced up at Phil and proclaimed, "this is not compulsary." He sensed Phil wasn't a catholic!

Pope Pious XII entered and this is how Phil remembered the meeting; Pope Pious XII (to Frank): . . . "And you my son, are a tenor?"

Frank: "No, your holiness, I'm a baritone."

Pope Pious XII: "Ah. And what operas do you sing?" (Phil bites his lip. This was no place for a laugh)

Frank: "I --- eh, don't sing opera, Your Holiness."

Pope Pious XII: "And where did you study?"

Frank: "I --- eh, never studied . . ." (The Pope looked him over quizzically: What are you doing here? Frank shrugged humbly. Phil now waited for Frank to explain the errors of the Catholic Church in Detroit. The Pope blessed Frank and turned to Phil. After all the travel Phil looked weary and a little hung over, a bit like Lazarus before he was warmed up.)

Pope Pious XII: " . . . And you, my son?"

Phil: "I am a comedian." (The Pope asks his Cardinal for a translation)

Pope Pious XII: "It is a blessed thing in these sad times to bring laughter." (He blessed Phil)

Phil: "I had the honor of seeing Your Holiness in Chicago, when you were Papal Secretary, at the Eucharistic Convention, I was playing a theater there . . ."

Pope Pious XII: "Yes, I have fond memories of America."

Phil: "Does Your Holiness know of Bing Crosby?"

Pope Pious XII: "Ah, yes!" (Obviously 'Going My Way' hadn't hurt Bing in the Vatican)

Phil: "He has four sons and I would like to take these rosary beads to him." (Phil brings out the beads)

Pope Pious XII: "You have three beads. Is there a Mrs Crosby?"

Phil: "Yes." (The Pope turned to the Cardinal, who added three mother-of-pearl Vatican-stamped beads to make a total of six. They were blessed. As they left, Phil put them down carefully into a tobacco can.)

Outside Frank Sinatra yelled at Phil, "You creepy bum! I take you to see the Pope - and you're plugging Crosby!"

Eventually Phil met up with Bing at the Kraft Music Hall and presented him with the blessed rosary beads.

"I want you to know that the last hand to touch these was the Pope's." Phil announced.

A perplexed Bing just shook his head and said, "Always kidding, everything's a gag."

Phil would go on to do USO shows with Bing too.

Alas, the partnership with Jo-Carroll didn't work out and they eventually went their own ways with a divorce in 1950. Phil said later that this marriage was spent mostly in Lindy's and Toots Shor's and cafeterias, Phil surrounded by almost everyone in the world except his wife.​​​​​​

1946 was a distressing year for Phil. In August, his great friend and mentor, Rags Ragland was set to renew his nightclub act with him at the Copacabana, when he began experiencing pain in his abdomen after returning from an alcoholic session after session with Orson Welles in Mexico. 

  1. Frankie, Phil and Rags
    Frankie, Phil and Rags
  2. Rags and Phil
    Rags and Phil
Rags Ragland was hospitalized. Frank Sinatra called in a specialist; however, the doctors determined that Rag's liver and kidneys were destroyed from years of alcohol abuse. ​​​

Rags would not leave the hospital alive. After falling into a coma, Rags died seven days later of kidney failure (uremia), three days before his 41st birthday. Phil and Sinatra were by Rag's hospital bedside. Many Hollywood celebrities attended Rag's funeral, including Sinatra, who sang at the service. 

Club operatives at the Copa insisted that Phil fulfilled his contract - but he didn't know if he could. Frank Sinatra told Phil, he could not make it as he was in the middle of filming It Happened in Brooklyn. After finishing a depressing dinner show, Phil sat anxiously in the dressing room. When he looked up he saw Frank standing there, smiling. He had flown in to play his stooge, to fill in for Rags (Frank and Phil had done the same routines during their USO tour). At the start of the next show Phil asked if there was anyone famous in the audience. He gave a signal to the ringside-seated Frank, who walked onto the floor. The crowd went berzerk. They clowned,  included Julie Wilson in one of their bits, and Sinatra sat down. The show brought down the house. Frank came back on stage to take a bow and Phil asked him if they could take one for Rags Ragland. It ended with Phil saying in tears, "May I take a bow for Rags." The audience was silent, crying in tribute to Rags. Frank Sinatra walked off a hero.

PHIL ON OPENING NIGHT AT THE COPA WITH SINATRA: Frank was in the middle of making a picture in Hollywood, but there he was standing in the doorway. I know Frank — you don't say, "Gee, you came." You play it cool. So I said, "Well, I'll do a few minutes first, and when I touch my tie you appear and we'll do our routines. You know them all." I can't tell you the reaction when he came out and I looked at him and said, "Scram, kid, I work alone." And then the standard jokes like, "I know there's a food shortage, but this is ridiculous," and "The blood bank is two blocks up the street," etc. We proceeded to do an hour and three quarters of material, and at our conclusion received an ovation. But gratitude embarrassed Frank. I looked for him to thank him for this expression of love and friendship, and he was gone—back to Hollywood, where he had caused a two-day delay because of this gesture. But that's Sinatra. You don't thank him. You just lean back and accept it. (This last passage © The Sinatra Family www.sinatrafamily.com)

Rags has 18 films to his credit mostly playing the good-natured oaf. He played opposite the likes of Judy Garland, Clark Gable, Abbott and Costello and Red Skelton. Before Hollywood, Rags was a trucker, a boxer and a movie projectionist. It was in his twenties when he entered the burlesque circuit. Like Phil, he became one of the house comics for Minsky’s. He quickly got a reputation for his wild ad-libs, his unpredictable intrusions into other comic’s acts, and his healthy off-stage libido which, by all accounts, could count star Minsky's stripper Gypsy Rose Lee as just one of his many conquests.

1947 was the year that Phil took off, big time, on the Broadway stage. Sammy Cahn and Jule Styne put together a stage musical, called High Button Shoes, that was based on the novel The Sisters Liked Them Handsome by Stephen Longstreet about his upbringing in New Jersey during the presidential years of William Howard Taft.  This musical treat really brought the best out of Phil.
  1. Sketch by William Auerbach-Levy (1889-1964)
    Sketch by William Auerbach-Levy (1889-1964)

This was one of Jule Styne's finest early musical scores, and was worth watching just for the fabulous Nanette Fabray and the hilarious Phil. The show was well received by the critics who singled out Phil and co-star Nanette for their superb performances.

The writers rewrote the musical when Phil got involved with the project. They built the plot around his previously minor character, Harrison Floy. The libretto for the merry show was rewritten by director George Abbott, who staged the musical in his typical rapid style which suited the characteristics of Phil, like hand-in-glove. Top choreographer, Jerome Robbins, was also on board the project.

Despite the show's promise, it struggled in out-of-town tryouts. This gave Phil the chance to ad-lib the show into the top league of hit shows.He drew on all his burlesque expertise and knowhow throwing in old routines he'd done in the 1930s with great brilliance.

Opening night: New Century Theatre, New York, October 9, 1947. 

The plot summarised:

Con artist Harrison Floy (Phil) and his shill, Mr. Pontdue (Joey Faye), arrive in New Brunswick, New Jersey, and hoodwink Mr. and Mrs. Longstreet (Jack McCauley and Nanette Fabray) out of some money from the sale of their property. Floy and Pontdue flee to Atlantic City with their ill-gotten profits but lose everything when Floy bets on the wrong football team.

In his second Broadway musical, Phils' clowning carried the evening, while Mrs. Longstreet was played vivaciously by Nanette Fabray (later Joan Roberts). Phil, as has already been stated, contributed to the script with his ad-libs; as he would later write in his autobiography, "By opening night, not one line of my part remained from Stephen Longstreet's original script." 

A highlight of the evening was the Tony Award–winning choreography by Jerome Robbins, in particular his farcical Keystone Kops ballet set on the beach at Atlantic City. Jerome staged this number in the manner of a Mack Sennett silent slapstick film. Full of sound and fury signifying nothing but hokum, this 20 minute roundelay is built around an old time cops-and-robbers chase through Atlantic City, with slamming bathhouse doors, squealing girls in frantic disarray and a jittery gorilla. It used the music of On A Sunday By the Sea, Liszt's Second Hungarian Rhapsody, and Offenbach's can-can from Orpheus in the Underworld. This number was so basic to the show that deleting it would render the evening incoherent. It was a major evocation of a period, a tribute to silent-film comedy. 

Robbins incorporated in his dance all the ingredients of the one-reeler: The mustachioed cops who jump straight up to register excitement, the wiggling bathing beauties with cupid-bow lips and goo-goo eyes, the slinking crooks of vaguely foreign origin. What evolves is a comic and skillful interpretation of Hollywood hoopla!!

High Button Shoes brochure
High Button Shoes closed on July 2, 1949, running for 727 performances. It transferred to the Shubert Theatre, NY and finally to The Broadway Theatre, NY during the run. In addition to Phil, as Harrison Floy, and Fabray (who was replaced by Joan Roberts in June 1948), the show featured Joey Faye. 

A London production opened at the Hippodrome on December 22, 1948 and ran for 291 performances.

Awards won:  

1948 Tony Award® Choreographer - Jerome Robbins  -  1948 Theatre World Award - Mark Dawson

Note: Sammy Cahn (1913–93) was one of Hollywood's most successful lyricists, but this was his only Broadway hit. The native New Yorker also wrote lyrics for the stage musicals Skyscraper (1965) and Look to the Lilies (1970).