Celebrity Entertainment Booking Agent - Headline Entertainment
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Kellie Pickler

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BIOGRAPHy

In 2005, singer Kellie Pickler landed a spot in the fifth season of American Idol. Though she finished sixth, the former waitress and Miss North Carolina contestant charmed audiences with her southern twang and blonde ambition, resulting in a contract with BNA Records that yielded her debut album, Small Town Girl, in the fall of 2006 and an eponymous sophomore release in 2008, which yielded Pickler’s first Top Ten hit, “Best Days of Your Life,” a song she co-wrote with Taylor Swift. Her third album, the Frank Liddell-produced 100 Proof, appeared late in 2011. She dropped the album The Woman I Am in 2013. Kellie Pickler, who was the first AI contestant to be cast on Dancing with the Stars, continues to tour the country.

 

Career Path

2005Charmed a national audience as a contestant on Season 5 of 'American Idol,' finishing sixth while her southern twang and backstory made her one of the season's most memorable personalities.
2006Signed with BNA Records and released debut album 'Small Town Girl,' which sold nearly 900,000 copies and produced three Top 20 singles including 'Red High Heels' and 'I Wonder.'
2008'Best Days of Your Life,' co-written with Taylor Swift, became Pickler's first Top Ten country hit, reaching number nine on the charts and featuring Swift on backing vocals and in the music video.
2011Released her Frank Liddell-produced third album '100 Proof,' a harder-edged artistic statement that signaled her evolution from 'Idol' ingenue to seasoned country artist.
2013Won Season 16 of 'Dancing with the Stars' alongside partner Derek Hough, scoring a perfect 30 on the finale freestyle as the first 'American Idol' alumni cast on the show.
2013Dropped 'The Woman I Am' on Black River Entertainment, her fourth studio album featuring three Pickler co-writes, deepening her creative ownership of her catalog.
2017Co-launched the nationally syndicated daytime talk show 'Pickler and Ben' with comedian Ben Aaron; the debut season earned three Daytime Emmy Award nominations including Outstanding Informative Talk Show Hosts.
2024Returned to the stage at Nashville's Ryman Auditorium for 'Walkin' After Midnight: The Music of Patsy Cline,' her first live performance since the death of her husband Kyle Jacobs, receiving a standing ovation from the crowd.
2024Made a rare television appearance returning to the 'American Idol' stage for a special episode celebrating the Class of 2006, her first national TV appearance in over a year.

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WHAT OUR CLIENTS SAY

Britney Z.
Chicago, IL
“Kevin Nealon was great. He was funny engaging and super nice with our guests and staff. Perfect for our audience. Thanks again for you all you help. We will call you again for next year’s event.”
Steven K.
Bronx, NY
“I can’t tell you how much I appreciate you sending Johnny Lampert to our company holiday party. Beyond his material, I am still blown how he so smoothly took control of the room and came up with great stuff on the fly. Rave reviews from everyone.”
Gary W.
Tampa, FL
“Lee Dewyze far exceeded my expectations! First and foremost, he was gracious and humble. He connected with the small group in a very personal way. He performed songs from his new album and did some unbelievable covers. His voice is incredible. My friends are still talking about how much they enjoyed his performance. Thank you very much for recommending him!”
Beverley A.
Fairfax, VA
“Thanks again for a job well done last Friday night. Our Entertainment Committee meets tonight, and the “Czar” has already let me know that he wants to schedule annaother comedy night at our country club for next year.”
Lynne K.
Trenton, NJ
“Thank you and Tom Cotter so much for making our event a great success. Your pick was excellent! Tom was an absolute delight to work with. Everyone loved him. Absolutely perfect! Thank you both so much!”
Kelly C.
Draper, UT
“Hi! Jeff Foxworthy was great! So funny and down to earth. He was showing photos of his grandkids, family and farm at the photo op after the show to everyone.”
Frank M.
Hauppauge, NY
“I’ve been hosting our golf outing for over 20 years. We’ve had some great comics over the years. Last night was a special evening with Tom Cotter. He had the audience railing. It was an outstanding success. He’s the real deal!”
Jeff H
Alpharetta. GA
“Thank you so much for landing Russell Peters for our meeting. He was amazing and, thanks to you, everything went perfectly. I have worked with others in the past scheduling talent for our meetings, but you were the best, by far. I look forward to working with you again. FIVE STARS!”
Temple Emunah Brotherhood
Lexinton, MA
“Thank you for the fine show you presented. We were a group ranging from 35 to almost 80 years old and the jokes were appropriate for our audience and in good taste. Audience participation was encouraged and this made the evening special. We look forward to your return for our next Temple Comedy Night!”
Chris H.
Lakewood, MD
“Thank you for the great performances last Friday night at our country club’s comedy night. All three acts really put on a great show. We are putting next year’s calendar together and I will reach out to secure more of your talents for sure.”
Wendy W.
Scottsdale, AZ
“You have proven to be a true partner to me and my organization. Everyone remarked that Tom Cotter was among the best live comedians they have seen. His pre-and-post show professionalism, onstage humor and the time he spent with our attendees afterward for photos was all very much appreciated. He was a pure pleasure to work with and a comedic force to behold onstage.”
Cathy R.
Scarsdale, NY
I wanted to send a Thank you to Piff the Magic Dragon. He performed at my son s Bar Mitzvah Saturday and he was a big Hit! Everyone enjoyed the show – the kids as well as the adult . He was very funny and very accomodating – We couldn’t be happier!”

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INQUIRE

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02
WE HANDLE
DETAILS

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03
ENJOY YOUR
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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

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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.

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