Win Tickets ($100): Macy Gray: On How Life Is 25th Anniversary Tour @ Crystal Ballroom | R&B + Soul

We are giving away a pair of tickets to Macy Gray @ Crystal Ballroom on July 14. To win, comment below on this post why you’d like to attend. Winner will be drawn and emailed July 7.



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From our sponsors
Macy Gray: On How Life Is 25th Anniversary Tour
July 14, 2025
6:30 pm doors, 8pm show | $50.50-$79.10 | All Ages
Purchase Tickets: crystalballroompdx.com

Crystal Ballroom
1332 W Burnside St, Portland, OR 97209

The ability to compose refreshingly candid music that resonates deeply with listeners isa rarity in music. Few artists possess this tool, however, R&B/soul singer-songwriter, musician, and record producer, Macy Gray, is one of them. With her vivacious voice, unshakable grip on soul, and funky spirit, Gray knows how to wield the power of music, which sets her apart from her contemporaries.

Originally from Canton, OH, Gray came to Los Angeles to attend USC for scriptwriting.While in school she started to write songs for her friends and found her voice when the singer scheduled to record the demos did not show up. That fateful day, a legendary career was born.

Gray broke into the music scene in 1999 with the release of her debut, triple-platinum album, ON HOW LIFE IS, she has become a powerhouse of R&B and Soul. She has amassed a devoted global fan base and sold over 25 million total albums globally. A five-time GRAMMY® Nominee, Gray received the GRAMMY® Award for Best PopVocal Performance in 2000 for her iconic song ‘I Try’ and has received two BRITAwards.

Now two decades into her storied career, the fully formed, multi-tiered artist has collaborated with brilliant musical mavens including Bobby Brown, Ariana Grande, andGalactic – just to name a few. She continues to be a force of nature on tour, as well and sells out venues in nearly every corner of the globe. Her talents also resound beyond music. She starred in Tyler Perry’s Black Reel Award-Winning Film For Colored Girls and has graced screens everywhere with her appearance in the show Brotherly Love and Cardboard Boxer and NETFLIX’s hit show Fuller House. Moreover, she made a now-legendary appearance in Training Day alongside Academy® Award winner Denzel Washington – one of many on-screen hallmarks.

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49 Comments

  1. Megan Comer on April 1, 2025 at 12:21 pm

    OMG! MACY yes please, i’d be honored to listen and attend!

  2. Lois Greenfield on April 1, 2025 at 12:22 pm

    I used to listen to her on repeat for ages but I’ve never seen her. I did have tickets for a show once but it was cancelled with very little notice (and I had already driven an hour to the theater) because she had a cold. (I guess her voice was more raspy than usual 😉) I would hope for better luck this time!

  3. teresa bergan on April 1, 2025 at 12:32 pm

    She was in my younger years and such a beautiful voice. Still powerful today! yes please

  4. Cory on April 1, 2025 at 12:34 pm

    Love me some Macy Gray

  5. Lindsay on April 1, 2025 at 12:35 pm

    I would love to see Macy Gray! I am excited that she is coming back to the West Coast!

  6. Nichole Christmore on April 1, 2025 at 1:17 pm

    What a perfect venue for Macy! Would love to join!

  7. Nicole SmithRyan on April 1, 2025 at 2:15 pm

    my childhood soul some dance and boogie

  8. Minda on April 1, 2025 at 6:12 pm

    Sweet Baby! Yes, let me introduce my 17 yo son to the “Time of my Life” Queen live, please. So fun. So powerful!

  9. Colette on April 1, 2025 at 6:19 pm

    Would love to see her live and surprise my sister who listened to her cd nonstop growing up. We all have a love for Macy because of her

  10. Anthea Proulx on April 1, 2025 at 11:56 pm

    She’s amazing. I’d love to see her live.

  11. James Rowell on April 2, 2025 at 6:54 am

    She is a fun talented woman,she has a voice unlike any other,love to see her

  12. Ellen Martin on April 2, 2025 at 8:23 am

    Can’t wait to see this

  13. CAROLYN I on April 2, 2025 at 10:40 am

    Oh this would be a good time! Good vibes!

  14. Meredith on April 2, 2025 at 1:35 pm

    Macy Gray has been with me in so many key moments- she’s a staple on the playlist of my life. Her whole vibe is infectious, and I would jump at the chance to experience her music live and at The Crystal Ballroom!

  15. Monique on April 3, 2025 at 2:00 pm

    I play it of but I’m dreaming of going

    • Parker on April 3, 2025 at 2:19 pm

      Aw this is going to be such a special show! I <3 Macy

      • Diane George on April 6, 2025 at 11:06 am

        Gotta say, I love Macy Gray!

  16. Paul on April 3, 2025 at 2:00 pm

    Saw her at Revolution Hall a few years ago. Great show.

  17. lisa on April 3, 2025 at 2:58 pm

    Macy is the best. Let’s get the party started!

  18. Glenn on April 3, 2025 at 3:06 pm

    love me some Macy Gray. Rhythm, blues, & soul for my soul!

  19. Danielle on April 4, 2025 at 7:58 pm

    This would be an amazing show to go to

  20. Matt on April 8, 2025 at 11:50 am

    Would love to win these tickets for my wife’s birthday.

  21. Val Liptak on April 8, 2025 at 12:04 pm

    What an awesome Summer Concert to look forward to! Summer’s comin’, Portland!!

  22. Amy K. on April 8, 2025 at 12:19 pm

    25 years already! This will be an amazing show.

  23. Stuart Kemp on April 8, 2025 at 1:38 pm

    Met her and band in 2004 or 5 My late wife loved her so much.My late wife’s son was invited on stage with his friend as they played “Hey Young World” .

    Would be awesome to relive if possible

  24. Amie Fipps on April 8, 2025 at 4:42 pm

    I have never seen her before. I know all the words to her songs.

  25. Mahsa on April 8, 2025 at 5:05 pm

    I love Macy Gray’s music and have never seen her live. Also, I’ve never been to a show at the Crystal Ballroom and would like to see what a show at that venue is like and experience the famous bouncy spring-loaded floors are like!

  26. Carol Trekas on April 8, 2025 at 6:20 pm

    Never saw Macy.

  27. TroyLynn Craft on April 9, 2025 at 6:24 am

    Would love to have the opportunity to see this Concert!

  28. Jill on April 9, 2025 at 1:04 pm

    This album was such a huge part of my early college days and I would LOVE to go see her! (A family friend’s son also used to play trumpet in her band back in the day…alas, no longer!)

  29. Lorraine Kaye Wesolowski on April 9, 2025 at 2:36 pm

    Oh I would absolutely love to see Macy!!! Thank you

  30. chris miller on April 10, 2025 at 2:24 pm

    She is a great performer and we like her sound

  31. Michael Duey on April 10, 2025 at 3:35 pm

    Such a great singer, comfortable in so many genres. The jazz album from a couple of years ago still blows me away. Love to see her live!

  32. Ashley B. on April 10, 2025 at 7:33 pm

    This will be unforgettable! What an amazing talent! Fingers crossed!

  33. Frank Byers on April 11, 2025 at 7:04 pm

    This will help me survive Pantera in August.

  34. Hunter M on April 11, 2025 at 11:27 pm

    The QUEEN

  35. Victoria Lopez on April 13, 2025 at 11:25 am

    What an awesome experience! Yes please 😍

  36. Vincent Durcan on April 14, 2025 at 11:44 am

    I would love to see this show!

  37. Lisa on April 15, 2025 at 12:00 pm

    Would be thrilled to see Macy Gray! One of my all-time favs!

  38. Valerie on April 15, 2025 at 12:21 pm

    I’ve loved Macy Gray since I was a child, and it’s always been a dream of mine to see her!

  39. Margaret on April 15, 2025 at 1:00 pm

    DYING to see Macy G LIVE!

  40. Kim C. on April 15, 2025 at 1:06 pm

    This would be such a fun concert!

  41. Paul Cook on April 15, 2025 at 1:21 pm

    Saw Macy at Revolution Hall a few years ago. Great show!

  42. Victor Enriquez on April 15, 2025 at 3:28 pm

    Would love to see Macy!!!

  43. Valerie Averill on April 15, 2025 at 8:11 pm

    Wow, this will
    be a magical eveing!

  44. Anastasiya on April 16, 2025 at 7:55 am

    Yes! What a voice.

  45. Mia on April 17, 2025 at 1:54 pm

    Would love to see her live!

  46. Denice Sheffer on April 17, 2025 at 6:52 pm

    Macy dear heart 💑 yes please 🙏 ❤

  47. Marty Sheffer on April 17, 2025 at 6:53 pm

    Macy Gray! What a lady !

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