Alan Jackson

BIOGRAPHy

After Garth Brooks, Alan Jackson is the most popular male country singer to emerge from the ’90s. Jackson’s hallmark is consistency – he writes many of his hits, and his way with a hook was part of the reason he has never hit a commercial dry spell, even into the new millennium. He also projects a modest, wholesome, down-to-earth image that made him one of the best-liked stars in country. The total package has resulted in an astounding 20 number one singles and 20 more Top Ten hits, all in the first 12 years of his career. The year 2001 brought an enormous hit in “Where Were You (When the World Stopped Turning),” a poignant attempt to make sense of the aftermath of September 11. It was followed by the full-length Drive in 2002, which spawned another number one in “Drive (For Daddy Gene).” The album was Jackson’s seventh to top the country charts, and it also became his first to top the pop charts. Jackson’s 17th studio album, Thirty Miles West, was released in 2012, followed by Angels and Alcohol in 2015. Alan Jackson performs live every chance he gets.

Career Path

1985Denise Jackson encounters Glen Campbell, leading to a songwriting contract for Alan Jackson.
1989Becomes the first artist signed to Arista Records' country division.
1990Releases his debut album, 'Here in the Real World'.
1991Becomes a member of the Grand Ole Opry.
1993Wins ACM Single of the Year for 'Chattahoochee'.
1995Awarded CMA Entertainer of the Year.
2001Releases 'Where Were You (When the World Stopped Turning)' and earns his first Grammy Award for Best Country Song.
2011Wins his second Grammy Award for Best Country Collaboration with Vocals for 'As She's Walking Away' with the Zac Brown Band.
2017Inducted into the Country Music Hall of Fame.
2021Publicly reveals his diagnosis with Charcot-Marie-Tooth disease.

Book Alan Jackson | Request A Quote

This site is designed for talent buyers interested in contracting artists for live performance at corporate, private functions and special events. Please be aware that all our contracts require pre-show secured financial commitments (binders and/or deposits).

We also regret that for legal and contractual reason we cannot respond to inquiries related to any of the following:

  • Requests for artist to play at non-paying fundraisers.
  • Requests to fwd. messages or for contact information.
  • Invitations to appear to accept awards, donate items for auctions, etc.
  • Requests for print, radio or TV interviews.
  • Upcoming public appearances of artist on the site.
  • Requests regarding TV or film projects.
  • Requests to forward jokes, songs, lyrics, etc.

In order for us to best understand your needs, we appreciate initial contact to be through the form below. If you prefer to speak with someone or your inquiry requires more immediate attention, please call us at 888.5526737.

Regular office hours are Monday–Friday, 10:00 AM – 7:00 PM (EST).

We typically respond within 24 hours

WHAT OUR CLIENTS SAY

HOW BOOKING WORKS

We make hiring top entertainment simple with our easy 3-step process.

01
INQUIRE

Tell us about your event,
date, and your vision
for entertainment.

02
WE HANDLE
DETAILS

We work directly with the talent’s team to negotiate
and coordinate.

03
ENJOY YOUR
EVENT

Relax and enjoy as we
ensure a seamless,
memorable experience.

WHY CHOOSE HEADLINE ENTERTAINMENT

20+

Years of industry
experience.

600+

Professional
Entertainers.

5,000+

Successful Events.

500

Trusted by Fortune
Companies.

Celebrity Entertainment Booking Agent - Headline Entertainment

PREMIER BOOKING AGENCY FOR CELEBRITY TALENT

Your trusted source for America’s top corporate comedians, musical acts, and celebrity entertainment. Our philosophy is simple: deliver exceptional acts and expert guidance to make your corporate event, fundraiser, or private celebration unforgettable from start to finish.

Our discerning eye for talent, industry experience, and impeccable service sets us apart. Using long-standing entertainment industry relationships, we secure the right performers for your event at the right price. From affordable local headliners to world-famous celebrities, we ensure your next corporate meeting, gala, fundraiser, or special event becomes the success you need.

Ready to book your perfect entertainment? Contact us today for a personalized quote.