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Music

Music sits at the heart of everything Jack Calloway does.

Working across classic jazz, swing and character-led performance, Jack appears as a bandleader, ensemble performer and solo artist, adapting each performance to the room, the audience and the occasion.

From high-energy cabaret to intimate live music settings, the focus is always the same: connection, atmosphere and craft.

The Midnight Creepers

Jack Calloway's flagship cabaret jazz ensemble

Built around a seven-piece cabaret jazz format, the band blends classic jazz and swing with sharp wit, storytelling and a strong sense of theatre. The result is a live show that feels as much like an event as a concert — playful, engaging and deliberately character-driven. ​ The project grew out of Jack’s formative years performing internationally, including time spent being mentored in New York, where the blend of musicianship, British humour and stagecraft quickly found an enthusiastic audience. That transatlantic influence remains central to the band’s identity. ​ While the ensemble has appeared under various names over the years, The Midnight Creepers represent the realisation of the band Jack first envisioned at the very start of his career — a long-standing project refined over more than a decade of performance. ​ Now performing internationally, the band is available in flexible line-ups to suit clubs, festivals, theatres and bespoke events, always delivering a show rooted in craft, personality and connection with the audience.

Bullet Highlights

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  • Established 2013 (13+ years of development)

  • Seven-piece cabaret jazz ensemble

  • International performances across the UK, Europe, USA and beyond

  • Influenced by early jazz, swing and classic cabaret

  • Character-led, audience-focused live shows

Ensembles & Projects

Bespoke & Commissioned Ensembles

Alongside The Midnight Creepers, Jack Calloway leads and curates a number of specialist ensembles dedicated to classic jazz, swing and British dance band traditions.

 

These projects allow Jack to explore different eras, formats and performance styles while maintaining the same focus on authenticity, presentation and audience engagement.

Featured Ensembles

Benny Goodman Tribute Band

A high-energy ensemble celebrating the music of Benny Goodman, focusing on the classic small-group and big band repertoire that defined the Swing Era.

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Pops’ Hot Five

A tribute to the early Louis Armstrong Hot Five and Hot Seven recordings, presenting early jazz in an energetic, accessible live format.

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The New Hylton Dance Orchestra

A 16–20 piece British Dance Band dedicated to the music of Jack Hylton, reviving the scale, style and spectacle of interwar dance orchestras for modern audiences.

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The Jack Calloway All Star Orchestra (debuting 2026)

A large-scale project bringing together a rotating selection of headline names from the worlds of jazz and classic bandleading for special concerts, festivals and touring performances.

In addition to established projects, Jack regularly assembles bespoke ensembles of varying sizes to meet specific briefs set by clients.

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These may range from small acoustic groups to full-scale orchestras, created for:

  • festivals and themed events

  • private and corporate functions

  • cultural and heritage projects

  • international appearances across the UK, Europe and the United States

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Each ensemble is built with the same care given to repertoire, personnel and presentation, ensuring performances feel intentional rather than generic.

International Artists & Collaborations

Jack regularly invites and hosts visiting and international artists for curated, ticketed performances, often presenting sell-out shows built around collaboration and shared repertoire.

 

These appearances form part of Jack’s wider commitment to creating distinctive live events that bring together musicians from different backgrounds, scenes and countries, offering audiences something unique rather than a standard touring package.

Solo Performer

As a solo performer, Jack offers an intimate, personality-led approach to live music.

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Drawing on a wide repertoire and years of experience engaging live audiences, these performances work particularly well in smaller venues, private events and curated evenings where storytelling and atmosphere are as important as the music itself.

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Solo performances can also be incorporated into larger events, acting as a focal point or linking element between other acts.

Guest Artist & Featured Appearances

Jack is available as a guest performer for one-off appearances, special projects and collaborative performances.

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This may include:

  • sitting in with existing bands or orchestras

  • appearing as a featured vocalist or instrumentalist

  • contributing to themed shows, talks or hybrid performance formats
     

These appearances are shaped collaboratively and designed to complement the wider event rather than dominate it.

© 2026 by Jack Calloway. All Rights Reserved. 

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