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Triangle Weekly Big Ticket Event Guide – Concerts, Comedy & Live Entertainment Across the Triangle

The Triangle is packed with major concerts, comedy shows, and live entertainment this week from May 18–25, 2026. From legendary artists like Sting, ZZ Top, and Pitbull to comedy favorites like J.B. Smoove and Funny Marco, there’s no shortage of big-ticket entertainment happening around Raleigh, Durham, Cary, Chapel Hill, Carrboro, and beyond.

Whether you’re looking for indie rock, country, reggae, comedy, orchestral performances, or tribute bands, this week’s lineup delivers something for every music and entertainment fan.

Monday, May 18, 2026

• 8:00 p.m. — ’68
  Local 506
• 8:00 p.m. — Future Islands
  Cat’s Cradle

Tuesday, May 19, 2026

• 7:30 p.m. — Clare Bowen & Jonathan Jackson
  Goodnights Comedy Club
• 8:00 p.m. — Sting
  Red Hat Amphitheater
• 8:00 p.m. — Josh Ritter
  Haw River Ballroom
• 8:00 p.m. — Pitbull & Lil Jon
  Coastal Credit Union Music Park at Walnut Creek
• 8:00 p.m. — Santigold
  The Ritz
• 8:00 p.m. — Future Islands
  Cat’s Cradle

Wednesday, May 20, 2026

• 7:00 p.m. — Distant
  Local 506
• 8:00 p.m. — The New Pornographers
  Haw River Ballroom
• 8:00 p.m. — Future Islands
  Cat’s Cradle

Thursday, May 21, 2026

• 12:45 p.m. — Throwback Sounds of Summer
  Rudy Theatre
• 7:00 p.m. — David Nail
  Bird’s Nest Listening Room
• 7:30 p.m. — Chicago
  Crown Theatre
• 7:30 p.m. — J.B. Smoove
  Goodnights Comedy Club
• 8:00 p.m. — Robber Robber
  The Pinhook
• 8:00 p.m. — Hiding Places
  Cat’s Cradle – Back Room
• 8:00 p.m. — Dakota Proctor
  The Pour House Music Hall

Friday, May 22, 2026

Friday’s lineup features some of the biggest shows of the week across the Triangle.

• Iration & Tribal Seeds — Red Hat Amphitheater
• ZZ Top & Dwight Yoakam — Koka Booth Amphitheatre
• ATLiens — The Ritz
• Funny Marco — Raleigh Improv
• J.B. Smoove — Goodnights Comedy Club
• The Secret Sisters — Fletcher Opera Theater
• A Tribute to Dylan and Cash — The Wake Forest Listening Room at Magnolia Roots
• Chris O’Connor — Room 861 at Goodnights
• On The Border – The Eagles Tribute Band — Lincoln Theatre
• Marisela — Raleigh Memorial Auditorium

Weekend Highlights: May 23–25

Saturday, May 23

• Carrboro Bluegrass Festival — Cat’s Cradle – Back Yard
• North Carolina Symphony: Sophie Mok – Tchaikovsky Piano Concerto No. 1 — Koka Booth Amphitheatre
• Comedy performances from Funny Marco, J.B. Smoove, and Chris O’Connor continue throughout the evening.

Sunday, May 24

• Jimmy Dore — Goodnights Comedy Club
• Caleb Caudle — Cat’s Cradle
• An American Celebration: The Music of John Williams — Koka Booth Amphitheatre
• Sydney Castillo — Goodnights Comedy Club

Monday, May 25

• 8:00 p.m. — King Garbage
  The Pinhook

Big Concerts & Comedy Shows Across the Triangle

This week’s Triangle Big Ticket Event Guide features some of the region’s biggest names in music, comedy, and live entertainment with events happening across Raleigh, Cary, Durham, Carrboro, Chapel Hill, Fayetteville, Wake Forest, and beyond.

For more concert announcements, nightlife coverage, comedy shows, and local entertainment news, visit  DoRaleigh.

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