Christmas My Way:

A Rat Pack Holiday Bash!

Created by David Grapes and Todd Olson

Arrangements by Vince di Mura


Production Requirements

2 Men & 2 Women


A Nightclub

It’s beginning to look a lot like a free fresh, knocked out, coo-coo, groovy Rat Pack style Christmas. Complete with 40 swinging hits, nothing will be silent in this night as 4 singers serve up cool versions of the Great American Songbook standards and holiday favorites. So, grab your bird, jingle your bells, pour a stiff egg nog, and invite your audiences to experience a Rat Pack Christmas!

Christmas My Way – Musical Numbers

Act I

Opening Collage
Mistletoe and Holly                                                            Don Stanford, Henry Sanicola, Frank Sinatra
I’ve Got the World on a String                                         Harold Arlen, Ted Koehler
Deck the Halls                                                                      Traditional/Thomas Oliphant
Jingle Bells                                                                             Traditional

The Christmas Duets
It’s Beginning to Look a Lot Like Christmas                  James Pierpont
Santa Claus is Coming to Town                                         J. Fred Coots, Haven Gillespie

The Sinatra Solo Set
The Gal That Got Away                                                        Harold Arlen, Ira Gershwin
Night and Day                                                                        Cole Porter
Chicago                                                                                     Fred Fisher
All of Me                                                                                   Gerald Marks, Seymour Simons

A New York Christmas
The Christmas Song                                                               Mel Torme, Robert Wells
Christmas Memories                                                             Alan and Marilyn Bergman
I Heard the Bells on Christmas Day                                  Gorden Jenkins, Edward B. Marks, Henry Wadsworth Longfellow

Closing Medley
Witchcraft                                                                                 Cy Coleman, Carolyn Leigh
All or Nothing at All                                                                Arthur Altman, Jack Lawrence

Act I

The Memories Medley
An Old Fashioned Christmas                                                 Sammy Cahn, Jimmy Van Heusen
I’ll Be Home for Christmas                                                      Kim Gannon, Walter Kent

The Moon Medley
I Wished on the Moon                                                               Dorothy Parker, Ralph Rainger
Ol’ Devil Moon E.                                                                         Yip Harburg, Burton Lane
Fly Me to the Moon                                                                    Bart Howard

The Twelve Days of Christmas                                                Traditional

The Winter Medley
Winter Wonderland                                                                    Dick Smith, Felix Bernard
Come Rain or Come Shine                                                         Johnny Mercer, Harold Arlen

The Farewell Medley
Be Careful It’s My Heart                                                              Irving Berlin
You Make Me Feel So Young                                                      Mack Gordon, Josef Myron
I Get a Kick Out of You                                                                Cole Porter

New York, New York                                                                    John Kander, Fred Ebb

Bows and The Christmas Song                                                  (Reprise)

My Way                                                                                             Paul Anka, G. Thibault, Jacques Revaux, C. Francois


Briskly directed by David Grapes, who co-created Christmas My Way with Todd Olson, the holiday musical revue intersperses show-stopping performances with bits of Sinatra trivia, anecdotes, a joke or two along the way. Oh, and there’s a hilarious audience sing-along to “The Twelve Days Of Christmas”—with new lyrics Sinatra himself might have penned.

There’s something for nearly everyone in Christmas My Way whether they be Sinatra fans or musical theater buffs or simply Angelinos in search of a couple of hours of holiday musical cheer. I had a Christmas ball at this Holiday Bash. You will too!

Grapes and Olson’s book is well-conceived and flawlessly delivered. At times touching and moving, it would make any crooner giddy with Christmas pleasure.

All in all, Christmas My Way possesses more depth, humor and sensitivity than many musicals and plays not simply because of its subject, but because those who created and performed it are inspired, interlocked and re-invented through it.

What a fantastic way to spend the holiday season with four miraculous singers/entertainers and the music of the number one singer of all time. Christmas My Way is a great big hit from start to finish, a Christmas present dressed to the nines and tied up with a bow!

Not only does the joint put you in a martini state of mind, but it’s a perfect location for “Christmas My Way,” a musical celebration of the season. But don’t get the wrong idea. This show, a holiday sequel to the successful “My Way” Sinatra piece, isn’t about melancholy holiday, crying in your eggnog, set ‘em up, Joe, sort of Christmas.

It’s a joy to the world from the very top floor celebration, featuring an incredible trio backing a quartet of excellent singers delivering mostly Christmas songs, performed at one time or another, by the Chairman.

You will recognize most of the nearly 30 tunes performed during the speedy show. Most are either holiday favorites or old friends from the Great American Songbook. What is more amazing is the enormous range of composers whose works are included in the piece. You get your Gershwins and Arlens and Kander and Ebbs, but you also get Henry Wadsworth Longfellow, who knocked out the lyrics to “I Heard the Bells on Christmas Day.”

Fun is a huge factor in this revue. During a Rat-Pack version of the “Twelve Days of Christmas,” the actors invite audience participation, making improvisation inevitable. Couple this with the hilarity of the revised lyrics and McLaughlin’s zest in conducting the song’s execution and suddenly the meaning of bash expands.

The music is meant to put an audience in a martini state of mind, nostalgic for old times and Christmases past and eagerly anticipating the song “My Way” which culminates the show.

The show, however, isn’t about melancholy or crying in your eggnog. Instead the quartet of excellent vocalists and trio of accomplished musicians are determined to light up the holiday with great music and spirit. If great music makes you happy, you’ll want to check out this gig.

Character Descriptions

Man #1 is aged 40-60 and should have a dark Italian look (the “rat pack” years).  Man #1 must have a deep/rich strong velvety baritone voice. He sings many of the standards from the Great American Songbook, so he needs to have an incredible vocal instrument and have a feel for phrasing and distinctive vocal style. He should dance or at the very least move extremely well. Tap dance skills are a big plus as there are a number of optional tap/dance breaks written for this character. Man #1 should also be able to sing close harmony. Ideally, this actor projects the style and easy sophistication WITHOUT DOING ANY SORT OF PHYSICAL OR VOCAL IMITATIONS. He is the leader of the ensemble in terms of setting the tone and style that the show’s music demands. Finally, he must relate well to the audience and possess the charisma to bring them along on this two hour musical journey into the world of “cool.”  This is the “key” casting decision and will be the most difficult performer to locate and cast.


Man #2 25-40 Is the skinny 1940’s big band “crooner” look. This actor should have all American boy good looks and be a physical contrast to the actor playing Man #1. He should have a strong legit lyric baritone voice and be an excellent part singer. He sings up to a G. Listen to the recordings with the Tommy Dorsey Orchestra to understand the smooth easy vocal style that is required for this role. Man #2 should also have a natural and unaffected flair for comedy as he carries much of the show’s humor and lighter moments. He spends much of the show trying to learn how to be “cool.” He is matched with Woman #2 and they need to look great as a pair.  Moves well.


Woman #1 30-50 should have dark, sensual, exotic, and striking good looks. In some ways, her character represents the female version of the (“rat pack” period). She is a “classy dame” who drips with style, sophistication, and class. Woman #1 has the more difficult singing role of the two women. Vocally she is a strong mezzo soprano who can also belt. Her vocal style is based on great “torch singers” like Ella Fitzgerald, Lena Horne, and Judy Garland. In other words, she performs with “balls.” This actress sings through a wide range vocally and must also be a capable part singer. A dark, smoky, husky sound is preferred. This actress must look good and match up well physically with Man #1.  One of the two women should be a strong dancer and the other move well.


Woman #2 20-35 should be a leggy blonde, brunette or redhead with drop dead looks and a smile that lights up the room. She should be able to project an energetic and youthful sexuality to the audience. Woman #2 is the type of woman that is represented in celebrities like Lauren Becall, Marilyn Monroe, Ava Gardner, Mia Farrow, etc. Vocally this character needs to have that same smooth liquid big band singer sound of the 40’s that Man #2 should also possess. Woman #2 is also a mezzo but does sing some soprano parts. Her voice should be lighter and provide a contrast to the darker sound required for Woman #1. She too needs to be a capable part singer.  For this role a strong dancer with tap skills would be a big plus. In the original production, Man #1 and Woman #2 were both outstanding tap dancers.  Woman #2 matches up physically with Man #2 and the two of them should make a handsome couple.


* Note:  Christmas My Way, the holiday sequel to My Way was originally intended to be done by the same cast as My Way

Creator’s Notes

Production History

The script and score currenly being licensed for production was revised in July of 2021 and is based on a highly successful Equity production that was directed by David Grapes at the El Portal Theatre in North Hollywood in December of 2012. Please do not add or cut any music. There is some leeway given with the script and jokes based on the information that you will find below. But always be judicious. If you want to write/create your own musical then do that. Please be respectful of our baby. David has directed nearly 20 productions of My Way and Christmas My way and he knows what works and what will fall flat. This piece will work as written, if you cast it properly, stage it well and allow the performers and the audience to have fun. Respect the music and arrangements and always honor the intent of the dialogue.

“What would have happened had The Rat Pack ever done a Christmas show?”

Well that’s the question around which this work was modeled.

And why, you ask? Lots of reasons. First, the holidays are a time when what we want most is to have a blast. And The Rat pack knew how to have a blast. But in the theatre what we usually do at Christmas time is tell sentimental stories or feel-good musicals. And we really don’t have that many different stories to tell in December. I mean once you get beyond Dickens and O’Henry and Dylan Thomas, December really belongs to the symphonies and their “Messiah”s and the ballets and their “Nutcracker”s. Our aim in creating this was to find something theatrical through which we could cut loose a bit with an event that was uniquely theatrical – a Sinatra tribute (because he was, as Count Basie called him, ‘the ultimate in theatre’). What also makes Christmas My Way uniquely theatrical is the ensemble, and the improvisational nature of this piece. Let me explain.

The Ensemble
The Rat Pack was one clean ensemble. In the theatre we wish our ensembles were as tight as The Rat Pack. Their banter was quick. They worked the audience like a top. Sometimes they were quickest not when a joke or bit worked well, but in the moments after it bombed. And sometimes they were so in tune with each other on stage – so keyed into the other performers, waiting for their next moment to leap into the fray – that the audience could just sit back and marvel at the fireworks. They listened keenly. They knew when to dive in and when to give way. Did I mention they had a lot of fun?

The Fun
How did The Rat Pack have a blast? The liquor? Maybe, though there is whole lot of evidence these days that what was in the bottles on that onstage bar was nothing but apple juice. So I doubt it was simply the drunk factor. The big thing was they liked each other: it was the camaraderie. They enjoyed each other’s company, and they loved what each other brought to the chemistry. So that was key. And they played with each other various ways. They had what was famously known as “the rib.” It was a good-natured shot, a put down, always accompanied by a smile, never a shred of malice. What is a challenge about this element these days is we tend to take offense much more than we did 40 years ago, and taking offense was never a part of The Rat Pack style. The shots offered in Christmas My Way ought not ever be mean, only delivered with a good humor among friends. Nothing is ever personal when it is among friends.

The Improvisation
They were also highly improvisational. They rehearsed with – yes you read that right – countless funny exchanges, jokes, and extended bits. So when you watch old footage of them in performance, some passages are fully scripted and rehearsed as we would Shakespeare. And the rest is sheer fly by the seat of your pants – working the audience, throwing curve balls at one another, LISTENING to the audience. So, rehearsed and impromptu at the same time.

The Content
And this is really important: what we have tried to achieve is a satisfying structure of the musical track, and between musical sections, an accurate sense of the Rat Pack comedy:
-how they interrupted each other
-how they reveled in jokes, stories, extended bits
-how they found ways to involve and “work” the audience
-how they would push the adult humor up to a point without getting truly risqué
-how they interjected stuff that they knew would get a rise out of their fellow performers
-how they upstaged each other by starting a song that was not theirs by singing spoof lyrics
-how they wildly leapt from topic to topic, eventually landing on an extended bit or musical number
And did I mention they had a lot of fun?

Some last quick words of advice relative to this text. Keep it fast (which is what all the interruptions and jokes/bits per minute ratio engenders), stay ahead of the audience, and don’t “help” the lines. Don’t play “She’s young and dumb and oversexed” while acting young, dumb or oversexed). The lines don’t need that help.

Finally, it’s the camaraderie. It’s tailoring it all to the four performers. It’s the fun. Good luck!

David Grapes and Todd Olson – 2021

Director’s Notes

The Setting
The setting should be “holiday-esque.” In most productions the set is designed to look very much like a sophisticated night-club. Others have given the production a very cabaret look. I imagine some future productions might even have a very Las Vegas-ssy look. So, as for literal setting, the set for Christmas My Way can and should be inspired by those things. Places in which great vocalists would have thrived and felt at home are the best choice. That said, “classy” has been a word tossed around a lot in the production reviews thus far. Even though it might be a cabaret, it needs to have a finished, glossy quality to it. An elegance. A dressed up feel. Also the trio should be on stage dressed in tuxes and in full view of the audience. There needs to be space for the singers to work at the piano and enough room to dance as couples. Add holiday touches as your space and budget allow (Christmas Trees, stacks of presents, bows, trim, Bells and ornaments etc.)

Stage Properties
A black or white baby grand piano
One to four functional retro (Sony) 50’s microphones
A fully stocked bar
2-4 sets of cabaret tables and chairs
Three bar stools
A tip jar on the piano
Various tall green plants and foliage plus any holiday decorations
A beautiful painted full moon that is flown in or hung during the moon medley

Sound is THE MOST IMPORTANT TECHNICAL ELEMENT of My Way. Sound reinforcement mattered to Sinatra and it will matter to your audiences. The cast sings 20+ vocal selections and it is vital that we hear the words and phrasing clearly without having to strain our ears. Vocalists of this era were true masters in the art of using a microphone in performance. Therefore, like Forever Plaid, Christmas My Way is intended to be performed using microphones as sound reinforcement. When possible wireless body mics should be used on each performer rather than using stand microphones. In addition to these microphones there should be one to four working “retro” Sony 50’s style microphones. Depending on the size of your theatre, you may also want to reinforce the piano or stand up bass. The show could also be performed using some variation of hand held microphones but I would make that a last option. My recommendation is to start sound rehearsals as soon as possible and locate the best sound engineer you can find to mix the show during each performance.

Pianist/Musical Director                                                                                                                                                                                                                                                   

This is perhaps the most important casting decision to be made for the production. This person controls almost everything about the production (tempo, style, energy, etc.). The perfect player would be an EXCELLENT sight reader, who not only has played musical theatre productions, but is in their soul also a jazz player. Much of the music is orchestrated in Sinatra’s favorite musical style, swing jazz. The score, while fully written out, is designed so that an accomplished musician can add his/her artistry to the performance. You need an outstanding player who is capable of managing the multitude of tempo, key and style changes that are written into the show’s medleys. On the other hand, a certain highly advanced skill level at improvisation is also extremely helpful. The original pianist/arranger/musical director, Vince di Mura, did not play the show the same way twice in over 300 performances and yet he never failed to support the singers or the dramatic action on stage. In many ways, this person becomes a fifth character in the production so look for a great musician who also has an interesting stage personality. This musician embodies the easy going Sinatra “cool,” He/she must be capable of assisting the cast members in finding this rather crucial albeit elusive quality in their performances. In all of our initial productions, this musician also served as Musical Director and conducted the stand up bass player and drummer from the piano during performance.

The musical score is constructed in a way that the music almost never stops. It was our intention that dialogue is given underneath solo piano in many of the “banter sections.” It is important the performance appears seamless to the audience. We also constructed the arrangements to delay any audience applause until certain key moments.

The show contains a number of optional dance breaks. Dance is a wonderful element and adds much to the production, if you have the talent to pull it off. Remember that Sinatra himself was a very good dancer.  The important thing is that the choreography be stylish and not call attention to itself. You’ll find when you look at the score little tributes to Astaire, Kelly, and others. The choreography should not look like traditional musical theatre choreography but rather social dancing that is motivated by the music and the location. It should posses class and style and look completely effortless. Never be afraid to let people stand still in a spotlight and “sell the song.” After all, these are some of the greatest tunes of the Twentieth century.

Character, theme, and style
Each of the four characters is unique. Each actor represents a different yet distinctive aspect of the music. Yet, the actors are also playing themselves. It is important that they feel comfortable enough to bring their own experiences to their role. You will also notice that we use direct address to involve the audience. One of the potential traps for a director is to let the musical become too “presentational” and too “audience centered.” You need to maintain the audience connection without sacrificing the “epic feel” of the piece. Remember it is a musical tribute and celebration of the Great American Songbookand not a cabaret performance in which each singer interprets the song in his or her own personal way. We are paying tribute to these vocalists and the reasons he recorded these great tunes in the first place. Keep it light, fast and fresh. The actors should be having just as much fun as the audience.

Whatever you do, do not let anyone do an imitation of anyone!!! That is a sure fire ticket to disaster. What is important is to have everyone connected to the production listen to as many of recordings of this era as you can get your hands on. Then get the performers to “channel” what they feel and hear from those recordings. Try to use the vocalists phrasing and musical sense whenever possible without imitating any idiosyncratic vocal mannerisms. You are after the essence, style, and cool of the way these artists interpreted a great song, not an exact duplication of their performances. The one thing I do recommend to you is enunciation. The music is always your guide and the arrangements your anchor. Cast great singers and then have them perform these wonderful songs with style and grace.

Additional Music
It is recommended that you do not use any recorded music during pre show or intermission.

Elegant sophisticated evening cocktail attire (Shorter dresses Act, I longer Act II. Must be able to move)

Holiday colors

White dinner jackets Act I
Black tux jackets Act II

Holiday vests and bow ties

The design should be romantic, sensual and moody. The production lends itself easily to the use of dramatic specials, gobos and break-up patterns. I prefer a white cyc in the background, which can be changed to various saturated colors. Two follow spots are recommended. You will be in need of some sort of lighting support for the moon medley. The lighting should be more theatrical than realistic and evoke mood rather than place.

Nothing sells a show like recognizable song titles. In your advertising, you may use any song title contained in the show. Remember, you do not have authorization or permission to use Sinatra’s picture, signature, fedora or likeness to advertise the production. These trademarks are owned now by Warner Music Group and their permission is required for use.

The best is yet to come – David Grapes and Todd Olson – 2021

Creator’s Bios

David Grapes II

David Grapes II


David is an Emeritus Professor of Theatre at the University of Northern Colorado, where he served as the Founding Director of the School of Theatre Arts and Dance and Producing Artistic Director for The Little Theatre of the Rockies for 15 years. David is also an award-winning director, actor, drama critic and playwright, and has provided administrative and artistic leadership for a wide variety of theatrical institutions including two professional regional (LORT) theatre companies. An active member of SDC, DGA and AEA his work as a stage director (250+ productions) and actor has been seen at major regional theatres across the United States. As a DGA member, David is the creator or co-creator of ten original musical revues, six plays, a screenplay, and numerous adaptations (, which have enjoyed over 500 productions worldwide. David holds a BA from Glenville State University (Alumnus of the Year 2010) and an MFA in Acting/Directing from the University of North Carolina at Greensboro. In 2021, he was inducted into The American Theatre College of Fellows at the Kennedy Center in Washington, DC.

Todd Olson

Todd Olson


Todd is the Executive Director for the Blue Ridge Community Theatre. His experience includes leading The Historic Palace Theatre, The Chattanooga Theatre Centre, and the American Stage Theatre in St. Petersburg, FL. He was the 2013 recipient of the Florida Professional Theatre Association’s Richard G. Fallon Award for “Excellence in Professional Theatre.” Todd has directed over 150 plays, musicals, and operas, including My Way (which he co-created) at the Actor’s Theatre of Louisville, and I Left My Heart (also co-created) at Milwaukee Repertory Theatre. As a playwright, his works include Casa Blue, the last moments in the life of Frida Kahlo, and Joe Corso Re-Enters from the Wings, which won the 2012 Holland New Voices Playwright Award at the Great Plains Theatre Conference and Althea & Angela. Todd received his M.F.A. from The University of North Carolina and is a graduate from the Institute for Advanced Theatre Training at Harvard. He was a teaching fellow at Harvard, and has taught classes at Vanderbilt, Boston University, University of North Carolina, and the University of South Florida.

Vince di Mura

Vince di Mura


Vince is a composer, arranger, jazz pianist and musical director; appearing on concert stages and theatres throughout North America, Canada, Europe and Latin America. He is currently the Resident Musical Director and Composer for the Lewis Center of the Arts at Princeton University, where he has served since 1987. He has conducted theatre seasons and fulfilled numerous compositional commissions at theatre across the U.S. His arrangements for Summerwind Productions include “My Way,” “Christmas My Way,” “Simply Simone” and “I Left My Heart.”  Mr. di Mura is also the author and curator of “A Conversation with the Blues:” A 14 part web instructional series on improvisation through the Blues, Produced by Soundfly Inc. Vince has 6 CDs on the market including his most recent release, “Meditations on the Sacred Heart.”  All of which are available at and any number of internet outlets. 



Conceived by David Grapes and Todd Olson
Book by David Grapes and Todd Olson

Original production directed by David Grapes
Original piano/vocal arrangements by Vince di Mura

First Workshop Production
MusicalFare, Buffalo, NY – December 2002
Directed by Randy Kramer

World Premiere Production
Birmingham Summerfest Cabaret, Birmingham, AL – December 2003
Directed by David Grapes

Special Thanks

Dr. K. Dawn Grapes
John Fredo

Christmas My Way – Videos

Christmas My Way – Audio

Opening Sequence

by Live at the Summerfest Cabaret

It's Beginning to Look a Lot Like Christmas

by Live at the Summerfest Cabaret

Act One Finale – Christmas Medley

by Live at the Summerfest Cabaret

Contact Us

Summerwind Productions, LLC – Box 430, Windsor, CO 80528          Email: