- Newport, KY
- Cover Band
- $3,000 – $6,000 per event
David Holloway Singer, Keyboard, Trumpet
Overview
Performance Options
David Holloway performs as a singer, trumpeter, pianist, and bandleader in formats ranging from a solo act to a 4-5 piece combo, a 7-8 piece dance band, or the full 14-17 piece Moondance Orchestra. His Jazz Catz ensemble specializes in Speakeasy New Orleans Riverboat Jazz, Swing, and Great American Songbook favorites. As a soloist, David sings country, retro rock, and pop with piano, trumpet, and flugelhorn with his own professionally produced tracks to create the sound of a full band in state of the art stereo. His 'Endless Times' DJ Service is available for a seamless, budget-friendly transition from live music to the latest tracks and dancing for all ages.
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Price range: Contact for pricing
Languages: English
Gig length: 110 - 300 minutes
What to expect
Punctuality and Setup
• On-time arrival: Show up according to the agreed load-in and soundcheck schedule—typically 2 to 3 hours before a full band performance.
• Self-sufficiency: Arrive with all necessary gear, cables, power distribution needs, and an assigned sound engineer (unless provided by the venue).
• Prompt teardown: Pack up and clear out efficiently once the set concludes per the venue's hard-out time.
Clear Communication and Logistics
• Advance details: Submit a clear stage plot, input list, power requirements (voltage/generators for outdoor spots), and green room needs well before the event date.
• Single point of contact: Band leader to coordinate day-of details with the event planner.
• Flexibility with the timeline: Adapt smoothly if speeches, dinner courses, or program elements run slightly behind or ahead of schedule.
Professional Presentation and Crowd Reading
• Appropriate dress code: Match the aesthetic of the event (e.g., black-tie formal, cocktail attire, or themed costumes) rather than showing up in casual practice clothes.
• Volume control: Respect venue noise ordinances and volume boundaries so guests can still converse during dinner or cocktail portions.
• Reading the room: Gauge the energy of the audience, manage smooth transitions between sets, and tailor the song selection to keep guests engaged on the dance floor
About
Biography, References and Venues
David Holloway is a singer, trumpeter, pianist, and songwriter specializing in Big Band Jazz, the Great American Songbook, and classic holiday music, but is equally adept in many genres, rock, country, pop, and funky horn band music as well. A Spotify and Apple songwriting artist and bandleader, David has entertained many corporate audiences in Louisville and throughout the United States, bringing timeless swing, smooth vocals, and expressive trumpet playing to stages from New York to New Orleans and beyond.
A prominent 50‑year member of a Jazz Big Band that originated in the 1930's, David continues to honor the golden age of jazz. He filmed the part of a 1932 ‘Speakeasy’ trumpet player for the Hallmark movie “Kentucky Roses” at world-famous Churchill Downs.
A retired computer analyst, David spends most of his time writing, producing and audio engineering music tracks using state‑of‑the‑art technology while collaborating with top‑notch studio musicians and vocalists.
Singers: Frank Sinatra, Tony Bennett, Harry Connick Jr., Dean Martin, Bobby Darin, and Michael Bublé — artists whose timeless style he treasures and performs.
David lives in Louisville with his cottage wife, Julie, and their beloved Shih Tzu, (pron. sheedzu) Bella. A gardener, wine & champagne grape grower, and lifelong dog lover — David brings that same warmth and joy to every performance.
Venues, cities, and shows:
Hallmark Movie 1930's Speakeasy scene jazz trumpet player
Anheuser Busch "Bud-Lite" TV ad - KY Derby call to the post trumpet solo
The Kentucky Derby Museum on “Oaks Day” - his Dixieland Band
Kentucky Derby Festival Mayor's Brunch 3 years @ Farnsley Moorman
Kentucky Derby Festival Steamboat Races
50-year member, 1930's Big Band “The Wednesday Night Big Band”
Maker's Mark Bourbon, Bill Samuels, Sr. Private Birthdays & Derby party
The historic 'Great Gatsby' Seelbach Hotel Louisville, KY
Jim Beam Bourbon International 200th Anniversary, Booker Noe
Humana Corp - Pres. David Jones - sang for his daughter's wedding
United States Naval officer's commission of the nuclear submarine "U.S.S. Louisville" Norfolk, VA
Kentucky Fried Chicken Corp, Colonel Harland Sanders (3) Birthday Parties
Brown-Forman Corporation
Caesar's Casino Showroom, Elizabeth, Indiana
The General Electric Corp
The Drake Hotel "Shepheard's Club" Park Avenue, NY
Cruise Ship Nassau-Bahamas
The New Orleans Country Club, New Orleans
The Olmstead, Louisville, KY
The historic Brown Hotel, Louisville
Bernheim Forest Arboretums
Corydon, Indiana Concert In-The-Park
Country Days Festival, Middletown, KY
Executive Inns: Louisville, Owensboro, Paducah, Vincennes, Evansville
The French Lick Hotel, French Lick, IN
Farmington (Lewis and Clark Historical site)
The Hershey Pocono Resort, Hershey, PA
Swiss Wine Festival, Vevay, Indiana
American Legion, The Elks, Moose and V.F.W.
Rainbow Division Of W.W. II Veterans
Louisville City - County Merger Celebration
Joe Huber Farms Starlight, IN
The Gaslight Festival, Jeffersontown, KY
Country Clubs & Boat Clubs in Louisville, KY
Hurstbourne Country Club
Big Spring Country Club
Wildwood Country Club
Woodhaven Country Club
Jolly Mon's Island Restaurant (Best of Louisville award)
Middletown Festival, Middletown, KY
Political party victory celebrations
WAVE-TV “Summer Fest”
W.C. Handy Blues Festival, Owensboro, KY
O'Shea's Pubs in Louisville, KY
Limon y Sal Restaurant
Mulligan's Restaurant Glenmary
I Love Tacos Restaurant Glenmary
Kingfish surround Glass Showroom & Restaurant Pavilion, Louisville
The Dr. Demento Show with "Weird Al Yankovic" Los Angeles, CA
David Holloway has performed in: New York City, “I'll take Manhattan, the Bronx and Staten Island too…" New Orleans, Dallas, Cincinnati, Norfolk, VA Greensboro & Hickory, NC, Ocean City, MD, Hershey, PA, Daytona, Panama City, Ft. Walton, FL, Salt Lake, Toledo, OH, Hampton/Virginia Beach, North Carolina, Owensboro & Paducah, KY, and Nassau, Bahamas, and Louisville, KY… where the good times flow at smooth as our Bourbon, the home of Muhammad Ali, Louisville Slugger Baseball Bats, and The Kentucky Derby!
Additional booking notes
Lighting, stage normally provided by the venue or client.
Sound provided normally by David Holloway.
Services offered
Set list
Artist Cover Guide (Song list below): David is constantly adding new song arrangements & requests and can perform songs in the original key from these male artists.
Andy Williams, Alan Jackson, Al Hirt, Andrea Bocelli, Barry Manilow, Billy Joel, Billy Paul, B.J. Thomas, Bob Seger, Bobby Darin, Bread, Brooks and Dunn, Bruce Channel, Bryan Adams, Charlie Rich, Chicago, Chuck Berry, Dean Martin, Delbert McClinton, Don Williams, Donnie Elbert, Dwight Yoakum, Eddie Arnold, Elvis Costello, Elvis Presley, Engelbert, Everly Brothers, Floyd Cramer, Frank Sinatra, George Jones, George McCrae, George Strait, Georgia Satellites, Hank Williams, Sr., Harry Connick, Jr., Harry Nilsson, Herb Alpert & the Tijuana Brass, Jack Jones, James Taylor, Jerry Lee Lewis, Johnny Mathis, Jimmy Buffett, Julio Iglesias, Kenny Chesney, Loggins & Messina, Louis Armstrong, Manhattan Transfer, Marty Robbins, Michael Buble', Mickey Gilley, Neil Diamond, Otis Redding, Paul McCartney, Perry Como, Ray Stevens, Ricky Nelson, Roger Miller, Ronnie Milsap, Roy Orbison, Smokey Robinson, Terry Stafford, The Beatles, The Drifters, The Eagles, Toby Keith, Tom Jones, Tony Bennett, Van Morrison, Willie Nelson, and more...
Partial Song List: includes some full big band arrangements
*Asterisk denotes songs written by David Holloway*
A Kiss To Build A Dream On, After The Lovin', Al Di La, All I Have To Do Is Dream, All In The Game, Amapola, And I Love Her, And I Love You So, Anniversary Song, As Time Goes By, Autumn Leaves, Banana Republics, Baubles, Bangles and Beads, Back Home Again In Indiana, Before The Next Tear Drop Falls, Besame' Mucho, Best Is Yet To Come, Blue Bayou, Blue Champagne, Blue Christmas, Blue Velvet, Brown Eyed Girl, Candy, Can't Help Falling In Love, Cathy's Clown, Change Partners, Changes In Latitudes, Cheek to Cheek, Cherry Pink & Apple Blossom White, Chinatown, Clarinet Marmalade, Colour My World, Come Fly With Me, Come Monday, Copacabana, Crazy, Cross My Heart, Crying, Danny Boy, Darlin', The Days Of Wine and Roses, Desperado, Do You Wanna Dance-Twist Medley, Dock Of The Bay, Don't Get Around Much Anymore, Don't The Girls All Get Prettier At Closin' Time, Desafinado, Didn't We, Don't Tell Me There Ain't No Santa Claus!* Do You Know What It Means To Miss New Orleans, Dream, Dreamsville, Dream Lover, Dream A Little Dream Of Me, Drinkin' Champagne, El Paso, Emperor's Waltz, End Of A Love Affair, End Of The World, Fascination, Fast As You, Favorite Melodies*, Feelings, Foggy Mountain Breakdown, Frenesi, Gentle On My Mind, Georgia, Get Me To The Church On Time, Ghost Of A Chance, Girl From Ipanema, Girl Talk, Gloria, Good Luck Charm, Great Balls Of Fire, Guantanamera, Handy Man, Happy Birthday, Happy-Happy Birthday Baby, Happy Trails To You, Hava Nagila, Have You Ever Really Loved A Woman, Hawaiian Wedding Song, Hello Dolly, Help Me Make It Thru The Night, Here Comes The Bride, Hey Baby, Hey Good Lookin', Hi-Heel Sneakers-Tom Jones Medley, How Insensitive, How Sweet It Is To Be Loved By You, Husbands and Wives, I Can't Get Started, I Can't Help It If I'm Still In Love With You, I Can't Tell You Why, I Concentrate On You, I Don't Know Why, I'd Get Along With My Neighbors* (If They Didn't Live Next Door), I Love This Bar, I'm So Lonesome I Could Cry, If, If I Didn't Care, If I Fell, I Had The Craziest Dream, I Go To Rio, I Hear You Knocking, I Just Can't Help Believin', I Left My Heart In San Francisco, I Never Had A Christmas Til You*, It Don't Mean A Thing, It's 5-O'Clock Somewhere, I Never Had A Christmas Til You*, I Just Want To Dance With You, I'll Remember You, I'm Getting Sentimental Over You, I'm So Lonesome I Could Cry, I'm Sorry, If I Could Be With You (One Hour Tonight), If I Didn't Care, I'm All Yours Tonight*, I'm Walkin', I Wanna Be Around, I Want To Thank You Baby, Imagination, In A Mellow Tone, Indian Love Call, Indian Summer, In The Still Of The Night, In The Summertime, Invitation, Isn't It Romantic, It Had To Be You, It's A Beautiful Day*, It's Impossible, It's Magic, It's Now Or Never, I've Got A Crush On You, I Want To Live Til I Die, Jamaica Farewell, Jambalaya, Jazz Me Blues, Juke Box Judy*, Just Can't Help Believin', Just In Time, Just The Way You Are, Kansas City, Keep Your Hands To Yourself, Kiss Her You Fool*, Knees Of My Heart, La Vien Rose, Ladyfingers, Last Tango In Paris, Last Waltz, Lazy River, Life Is A Beach*, Love For Sale, Love Me Tender, Love Me With All Your Heart, Quando Caliente El Sol), Lover Man, Mack The Knife, Make The World Go Away, Mambo Italiano, Margaritaville, Maria, Masquerade, Meditation, Mexico, Misty (standard & Ray Stevens), Michelle, Moondance, Moon Glow, Mood Indigo, Moonlight In Vermont, Moon River, Mountain Laurel*, My Blue Tattoo*, My Buddy, My Funny Valentine, My Old Kentucky Home, Nadine, Near You, Never On Sunday, Night and Day, Night Life, No Shoes No Shirt No Problem, Now I Know What A Love Song Means*, Ob La Di, Old Time Rock And Roll, On An Evening In Roma, Once In A While, One Christmas Wish*, Only Love Can Break A Heart, Only The Lonely, Only You, Ooh Baby, Baby, Our Love Is Here To Stay, Perfidia, Poor Butterfly, Pretend, Pretty Woman, Quando Caliente El Sol, Quiet Nights, Quizas, Remember When, Rocky Top Tennessee, Round Midnight, Saint Louis Blues, Satin Doll, Second Time Around, She (Elvis Costello from the movie Notting Hill), She's Always A Woman, She's Got The Rhythm, Since I Don't Have You, Since I Fell For You, Sleepy Time Gal, So Nice (Summer Samba), Some Beach, Somethin' Stupid, Somewhere In My Broken Heart, Somewhere Over The Rainbow, Somos Novios, Strangers In The Night, Sugar Blues, Summer Wind, Suspicion, Sway, S' Wonderful, Tangerine (trumpet), Teddy Bear, Tenderly, Tennessee Waltz, That Cat Is High, That Sunday That Summer, That's All That Matters To Me, The Chair, The Christmas Song, The Good Life, The Last Date, The More I See You, The Shadow Of Your Smile, The Things We Did Last Summer, The Way You Look Tonight, The World We Knew, Then You Can Tell Me Goodbye, Til There Was You, Tiny Bubbles, To All The Girls I've Loved Before, Too Marvelous For Words, Travelin' Man, True Love Ways, Tulsa Time, The Twist, Unchained Melody, Unforgettable, Up On The Roof, Venus, Venus (She's Got It), Watermelon Man, Wave, We Really Shouldn't Be Doin' This, We've Got Tonight, What A Wonderful World, What's Your Name, When I Fall In Love, When It's Sleepy Time Down South, When The Saints Go Marchin' In, When You Wish Upon A Star, Where Did Our Love Go, Willow Weep For Me, Wimoweh (The Lion Sleeps Tonight), Wine Spo-dee-oh-dee, Witchcraft, Yellow Bird, You Belong To Me, You Don't Know Me, You Go To My Head, You Never Can Tell, You'll Never Know, Young At Heart, Your Mama Don't Dance…
Influences and inspiration
Singers: Frank Sinatra, Tony Bennett, Harry Connick Jr., Dean Martin, Bobby Darin, and Michael Bublé, and many others:
Draws inspiration from the great songwriters:
Edward Chester Babcock (a.k.a. James Van Heusen) & Sammy Cahn, Cole Porter, Irving Berlin, Harold Arlen & E.Y. Harburg (Over the Rainbow), Johnny Green, George Gershwin, Duke Ellington, J. Fred Coots, lyrics by Haven Gillespie, Jerome Kern, Johnny Mercer, Hoagy Carmichael, Richard Rodgers, Lorenz Hart, Oscar
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