Big Bossman Entertainment

09/01/2026

Been slacking on posting lately..😅 Will be posting the updated schedule soon.

08/14/2026

Hey Colorado Springs Big Bossman Entertainment is Hosting Karaoke every Thursday and Saturday night from 8 p.m. till midnight and don't forget to get to grab your $25 gift certificate ($50 total value)

The Boulevard

08/07/2026

Tonight, we are coming together for food, fun, and fundraising. VFW 6461 Auxiliary is hosting a complete $12 Fried Chicken dinner, followed by a night of karaoke at the post.
Every song you sing and every plate we serve helps support the Pikes Peak Young Marines on their historic trip to Pearl Harbor. Come out and show your support for our youth, our heroes, and our community. See you there!

07/25/2026

Ready to level up your weekend plans? 🕹️🎤
Step inside The Control Room and take the mic! We’re blending classic arcade vibes with high-energy karaoke all weekend long. Whether you're trying to hit the high score on stage or just cheering on Player 1, this is where the weekend happens.
Here is your weekly quest log:
👾 THURSDAYS
6:00 PM – 8:00 PM: Bingo Trivia (Warm up your brain gears!)
9:00 PM – Midnight: Karaoke Unlocked (Take the stage!)
🎤 FRIDAYS
9:00 PM – 1:00 AM: Late-night Karaoke action. Grab the mic and dominate the leaderboard!
🌟 SATURDAYS
9:00 PM – 1:00 AM: The ultimate boss level. Pure karaoke energy to close out the weekend!
No quarters required to sing—just bring your favorite tracks and your crew. See you at the main console! 🚀

07/25/2026

🎤 SATURDAY NIGHT KARAOKE AT CHELSEY’S! 🎤
Hosted by Big Bossman Entertainment
Ready to grab the mic, belt out your favorite tracks, or just kick back with awesome food and cold drinks? Join us every Saturday night for the ultimate neighborhood hangout!
Whether you're a seasoned performer or a shower singer, come as you are for good vibes, great music, and epic Saturday night specials.
🗓️ When: Every Saturday | 8:00 PM – 12:00 AM
📍 Where: Chelsey’s Wings, Burgers & Spirits
📍 Location: 3535 N Carefree, Colorado Springs, CO 80917
🔥 SATURDAY NIGHT FOOD & DRINK SPECIALS 🔥
🍔 Cheeseburger Combo – $15
Juicy cheeseburger, golden fries, and a soft drink
🍗 Wings & Beer Deal – $15
8 delicious chicken wings + a cold schooner of beer
🍔 The Burger Pack – $30
4 burgers + 4 orders of fries (perfect for sharing with your crew!)
🍹 $3 Drink Deals
$3 Well Drinks & $3 Drafts all night long!
No sign-up pressure, no hassle—just high-energy karaoke, great food, and good people.
📞 Questions? Call Chelsey’s at (719) 247-8618
Tag your karaoke partner and we’ll see you this Saturday! 🎶

07/20/2026

Calling all Outlaws and Aspiring Vocal Superstars! 🎤🤠
Read the warning on the package carefully, folks, because Big Bossman Entertainment is NOT legally responsible for the sudden surge of happiness you’re about to experience at Counterfeit Cowboy’s Karaoke night. 🤣
Mondays are for rebels, and we're taking back the night. The mics are live, the stage is yours, and the only requirement is that you sing LOUD! Whether you’re a line dancing professional or just here to two-step in place, the floor is open for dancing until midnight.
The best part? Our drinks are reasonably priced, so you can afford enough liquid courage to hit that one high note in ‘Friends in Low Places’. (We even have cold Bud Light and Coors waiting in the cooler – those neon signs are real, even if our cowboy accents are counterfeit! 🍻)
Don’t just sit at home; come live country with us. New friends are guaranteed, and the loss of inhibitions starts at 9 PM sharp. Grab your boots and your friends – it’s time to karaoke responsibly!

07/19/2026

Karaoke at Chelsey’s! 8-12 come sing some songs with me!!!

07/16/2026

Ready to have some fun this weekend! This week and Control Room kicks it off on Thursday night from 6 to 8 with bingo trivia. Followed up with karaoke from nine to midnight and then karaoke Friday and Saturday nine to one. It’s time to level up your karaoke!