It’s been a busy holiday break for Chicago-based musician Carey Deadman. While most of us were stuffing ourselves silly with cookies and reruns of “A Christmas Story,” he spent the break fixing musical arrangements  for Drury Lane Oakbrook’s latest show, Spamalot, which recently began performances. And while doing that, he’s been trekking to the Cadillac Palace Theatre each night to play lead trumpet in the pit at the Chicago stop of the first national tour of Wicked.

But this is how he likes it. A self-admitted workaholic, Deadman has been the premiere music arranger for many big shows in Chicago — particularly at Drury Lane Oakbrook, where he’s served as their resident music arranger since 1996.

How much of a workaholic is Deadman? Well, chances are if you’ve seen a Broadway in Chicago musical, you’ve heard him in the pit. As recent examples, he played trumpet in Jersey Boys during its multi-year run in Chicago (and even appeared onstage at the show’s finale to wail on “Who Loves You”), he played lead trumpet in the pre-Broadway tryout of The Producers at Chicago’s Palace Theatre (now the Bank of America Theatre), working with Mel Brooks and orchestrators Doug Besterman and Larry Blank. And, more recently, he played in Shrek, the Musical — as well as a number of others.

But beyond playing in the pit, Deadman is a master music arranger. If you caught Drury Lane’s magnificent production of Ragtime earlier this summer, he was the one who managed to take the show’s 20-plus orchestra arrangement and make it sound like a million bucks with just 10 players (the maximum size the Drury Lane’s pit can hold).

And, interestingly, Deadman and I both graduated from Alpena High School and participated in the AHS band (I played second and first horn while he first chaired trumpet — we just missed each other by 20 years). He then went on to study jazz performance at North Texas State University, and then acquired his masters in brass performance and pedagogy at Northern Illinois University, which brought him to Chicago in the mid ’80s. From there, he quickly found steady work playing a number of gigs at various clubs and gained a reputation as the go-to trumpet player.

I had the opportunity to meet Deadman and talk about his exciting career over a glass of wine and dinner at Petterino’s last week prior to an evening performance of Wicked, where he shared stories of working with Sinatra and a few Chicago jazz legends. He then graciously invited me to tag along with him backstage at the Caddy Palace to see the Wicked pit, meet a few of the musicians and watch him warm up for that evening’s show — his last before devoting his time to Spamalot. Unfortunately, due to issues out of our control, I couldn’t stay to watch the performance from the pit, but he invited me to sit in a music rehearsal of a Drury Lane show, and I very much look forward to that experience and sharing it here.

In the meantime, here are highlights of my conversation with Deadman:

Musician, arranger, producer — out of all the things on your resume, what’s your favorite thing to do?
I love it all, but I really get the most satisfaction playing the trumpet. It’s the most natural thing I do.

When you play in a pit orchestra, don’t you get bored playing the same music night after night?
Not at all. The goal is to play the score better than you played it the night before. And when you’re a perfectionist like me, it’s a challenge. And that’s not just my view — all the players in the pit in Broadway in Chicago shows take this job very seriously. We have some of the best musicians in the country in Chicago, and playing in the pit is one of the best gigs to have as a professional musician in this city. It’s steady work, and the job is a creative challenge.

Out of all the shows you’ve played, what’s your favorite as a trumpet player?
Oh, that’s a good question. Wicked is a challenging show to play. Fosse was also fun, thanks to that big solo in “Sing, Sing, Sing.” I also enjoyed playing in Movin’ Out, Jersey Boys and Ragtime.

What inspired you to become a musician and music arranger?
I came from a musical family — my father owned a music store in Alpena, and my grandfather hosted a Saturday night radio show in Alpena called “Melody Lane” and tuned and rebuilt pianos for a living. I also played trumpet in high school, and when I saw legendary trumpet player Bill Chase in a concert at my school, that was a huge inspiration for me. In Dallas, I studied trumpet with Don “Jake” Jacoby who gave me the skills necessary to be an excellent trumpet player. This really propelled my career. I think about Jake every day.

Can you tell me a bit about how you arrange music for a Drury Lane show?
Sure — Drury Lane wants all their shows to look and sound like a million bucks, while also keeping ticket prices affordable. So, we have to be judicious about how many players we want in each show. For shows with big, sweeping scores, like Sweeney Todd, which we’re doing next season, we’ll have a larger number of players. For shows like Seven Brides for Seven Brothers, we used a smaller ensemble. I then rework the score to accomodate the number of musicians, using the instrumentation we have on hand to the fullest effect. The music director will then work with me to fine-tune the sound of the show. For example, in Spamalot, I got an email from the music director today saying that a passage in the show sounded a little thin, so I’m going to fix that. I also have a full-time assistant and copyist who help compile and print out my arrangements for the players.

I see on your resume you worked with Frank Sinatra. Any good Sinatra stories?
Yes, I played in nine tours with Sinatra in the early ’90s. He was very professional. We didn’t see much of him, to be honest. He would travel by private plane, and then arrive at the venue with his cavalcade and police escort just before showtime. After his final bows, he would leave the same way he arrived as we were playing his exit music. He would literally be on the road before we got done playing our last note in the show. I also recall rearranging a section of “Fly Me To the Moon” to rework a cut to the song — which we called “the shout section” — that I felt needed reinstated and presenting it to Sinatra. I guess he liked it, because he used it in his act from that point on.

What information would you give to an up-and-coming musician who wants to break into the professional scene?
It’s pretty simple: show up on time, be accountable for yourself and play well. There’s no need to try to sell yourself; let your playing do the talking. If you’re good at what you do, and take it seriously, word of mouth will spread, and you’ll get noticed. And perhaps you’ll be asked to sub in a show.

Added bonus: photos from the Wicked pit:

Deadman arrives at the theatre an hour before showtime to set up his stand, review the music, and warm up.

A shot of the trumpet score for the opening number in Wicked. Note that Deadman has added the notes “Not too slow” above the first measure, and “not too fast” above the sixth measure. These reminders, Deadman explains, were necessary after having performed the score a different way when he played trumpet in the sit-down Chicago production of Wicked (which closed two years ago). But in this tour, the new conductor’s tempi are different. Also, you’ll see it says “[London]” at top of the score. This is because if a change in orchestrations is made when opening a new production of Wicked, those changes are universally adopted across all other productions. So, the national tour is using the London orchestrations for the opening number.

From the Cadillac Palace orchestra pit — 30 mins to showtime.

With about 20 mins to showtime, Deadman goes into the bowels of the Cadillac Palace for a final warm up.

Showtime!