Win Tickets ($100): Macy Gray: On How Life Is 25th Anniversary Tour @ Crystal Ballroom | R&B + Soul
We are giving away another 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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OMG! MACY yes please, i’d be honored to listen and attend!
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!
I would LOVE to see her live!!! And it’s on my partner and i’s anniversary <3 it would be so special. We listen to Macy all the time.
She was in my younger years and such a beautiful voice. Still powerful today! yes please
Love me some Macy Gray
I would love to see Macy Gray! I am excited that she is coming back to the West Coast!
What a perfect venue for Macy! Would love to join!
my childhood soul some dance and boogie
Sweet Baby! Yes, let me introduce my 17 yo son to the “Time of my Life” Queen live, please. So fun. So powerful!
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
Macy is the best. 😊
She’s amazing. I’d love to see her live.
She is a fun talented woman,she has a voice unlike any other,love to see her
Can’t wait to see this
Oh this would be a good time! Good vibes!
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!
I play it of but I’m dreaming of going
Aw this is going to be such a special show! I <3 Macy
Gotta say, I love Macy Gray!
Saw her at Revolution Hall a few years ago. Great show.
Macy is the best. Let’s get the party started!
love me some Macy Gray. Rhythm, blues, & soul for my soul!
This would be an amazing show to go to
Would love to win these tickets for my wife’s birthday.
What an awesome Summer Concert to look forward to! Summer’s comin’, Portland!!
25 years already! This will be an amazing show.
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
I have never seen her before. I know all the words to her songs.
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!
Never saw Macy.
Would love to have the opportunity to see this Concert!
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!)
Oh I would absolutely love to see Macy!!! Thank you
She is a great performer and we like her sound
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!
This will be unforgettable! What an amazing talent! Fingers crossed!
This will help me survive Pantera in August.
The QUEEN
What an awesome experience! Yes please 😍
I would love to see this show!
Would be thrilled to see Macy Gray! One of my all-time favs!
I’ve loved Macy Gray since I was a child, and it’s always been a dream of mine to see her!
DYING to see Macy G LIVE!
This would be such a fun concert!
Saw Macy at Revolution Hall a few years ago. Great show!
Would love to see Macy!!!
Wow, this will
be a magical eveing!
Yes! What a voice.
Would love to see her live!
Macy dear heart 💑 yes please 🙏 ❤
Macy Gray! What a lady !
Macy Gray was my favorite music growing up. I love her music so much! It would be such a delight to win tickets to see her 🙂
Would love to see her again!
My wife and I both love her voice and her music 🙂
Macy Gray’s music has been the soundtrack to some of the most important moments in my life. Her voice is raw, soulful, and full of truth—the kind that reaches inside you and stays there. My partner and I have weathered a lot together, and this year especially, we’ve been holding each other through grief, growth, and big transitions.
We don’t get a lot of chances to just be—to step out of survival mode and into something joyful. Seeing Macy Gray live would be one of those rare, healing moments where we could exhale and reconnect with the parts of ourselves that still dance, still dream, and still believe in magic.
We’re not just fans. We’re people who’ve leaned on her lyrics when we couldn’t find our own words. Winning these tickets wouldn’t just be a night out—it would be a moment of joy that we really, truly need.
Thank you for considering us 💛
Iconic
Macy Gray! oooo Yes!
I can’t walk away.
This would be such an amazing date!
Oooooooooh! Yea baby, pick me.
Ummmmmmmm, please? lol
Would love to see her in person!
I would really enjoy her performance. One of the few choices I can say is mine..choice of musical artists.
Wowza! Such a great artist! An amazing talent! Would love the privilege of attending her concert!
Yes please!
I would love to take my BFF. We are both on a budget these days and sadly cannot afford such luxuries right now. This would be a treat for sure.
Amazing voice
Sounds super fun!
Oh wow!! I’d LOVE to see Macy Gray just once. I listened to her first CD on repeat!!
Oh this would be a treat! Add my name to this looong list, please.
‘sI bet she is amazing live! I’ve loved her music since I heard it back in the 90’s
Saw her front row in Salem – love to see her again.
Please and Thank you
Remember watching her music videos on TRL :p
OMG! Missed Macy when she performed at the Elsinore Theatre awhile back.. Words I would use to describe Macy Gray are: soulful, funky, vivacious, unshakeable, forthcoming, multi-talented, a force of nature … need I say more? Would love to finally see her at my favorite historic venue, “The Crystal Ballroom” with its floating dance floor, vaulted ceiling, and grand chandeliers.
MACY GRAY?!?!?!? Look, as a young person who’s barley been able to experience live music, never been to this venue, and might never get this chance again I’m literally begging you ! Hfjdsbhedgfdj
My middle school heart is swooning 🤩
Macy Gray! Would be an amazing day! First time seeing her okay!
Such an intoxicating voice. Hoping to see her in person.
Haven’t heard her for awhile.
I would love, love, love to see Macy Gray!!
Please count me in!
My lovely dog is named Macy in honor of this music and love, I would love to attend
I love her style! I’m also a Soul Singer and she inspires me always…this would be a dream come true and help my training as a Soul Singer 💖🎶
Ok, I have to win for my friend. MASSIVE Macy fan. I’m talkin’ big.
Would love to see Macy Gray rock the house. She’s amazing XO
Macy gray!!!! So ooooo excited just to even imagine her live on stage. I’ve lived her since I was 18 years old and I’ve never stopped. Dancing, singing along with her songs and having fun with ask the other people that know and love her. It woukd be amazing. Shows are made for people like me. I’d love to go break my streak of not getting out at all with an epic singer like Macy gray. I don’t think I’d do smiling all night long. 😀
I have always wanted to see Macy Gray live in concert. This would be a dream come true!
Macy Gray the queen!!!
I would be honored and thrilled to get the chance to see Macy in Portland!!
Her first record was amazing! I would love to see her live!
Macy Gray is one of the most underrated artists of today! It is a dream of mine to see her live!
She is a spit fire talent, and I would love these tickets.
Macy is awesome!
I’m in my “go to all the concerts. ALL THE CONCERTS” era, and I’ve never seen Macy before!
I would love to go, I love music but I have NEVER been to a concert before. And I would love to see an artist that was good as Macy!
Because in 1999, I tried to sing ‘I Try’ in the car and nearly got kicked out of my own family.
Redemption is overdue.
Would love to go 💜
Love Love Love Ms. Macy
Because I want to take my bestie 🥰 and we LOVE Macy
25th anniversary. Lets go. Yes please.
Oh my goodness, I’ve loved Macy Gray since the beginning, 25 years!!! This single mom and 7th grade science teacher would be ecstatic to go!
Would love to see her live
Would love to experience hearing her Beautiful Voice In person. And after the year I’ve had almost becoming homeless due to my Depression over the loss of my boyfriend to cancer. This would bring me Closer to Feeling him watching over me. 🤞💜
Oh my Macy! I saw her show on NYE in San Francisco about 20 (+) years ago and have never forgotten the energy of that experience! My friends and I choreographed dance moves to her songs in college and I still rock them whenever I play her music.
Love Macy Gray! It would be an honor to see her perform life.
This will be an amazing show!
Macy Gray is one of my all time teen favorites! I used to listen to her on repeat and would love to see her live
Awww it would be so nostalgic and healing to see Macy!! I’d love to go to this show!
Yes
I would be so grateful to win!!!
I probably won’t win as there are a million other people commenting on this, but it would be really cool to get free tickets to this show.
I love Macy Gray. Her voice is gold. Would love to hear her sing.
She is the best.
nothing fancy other than i would like some free tix 🙂
I love Macy Gray!
So many memories made to Macy Gray songs!! Would love to relive them in Portland!
Would LOVE a night out to see Macy Gray!!
Among other things , we have videos of our (now 20 something ) year old daughter dancing to her music. Been listening to Macy Gray for that long !!
Would be fun to see her again. Saw her in Boise about 15 years ago than after the concert she DJ at a club
25 years?! This would be so cool to see her live. Love her stuff!
i have always wanted to see her live. her sound hits my soul!
Pick me
Her music brings me back!
what a soulful voice- i would love to attend!
Oh wow! Amazing!
What a perfect venue for Macy! Would love to join!
Fun Times! Yes, please and thank you!
Looking forward to winning this one! 🙂
This is going to be a great concert to go too, please
Grew up listening to Macy! Stoked she’s headed to Portland!
I heard Macy Gray for the first time in 2000 or 2001 and never thought it will be 24 years later with a chance to go!
We would love to see Macy Gray!!
Love Macy Gray, would be most excellent to see her live.
Would love to see Macy!
A legend and an icon, this would be such a fabulous opportunity!
love Macy!! I would be so grateful for tickets.
Yes please!
Absolutely LOVE her and have listened to her music since she came out!! Would love to see her live!
Macy Gray is one of my favorites. Her voice is like stress relief. Would love to listen to her live
Macy, Macy, Macy, how I’d love to see thee! Yes please and thank you for an opportunity to win tickets!
Each of these responses are good and all should deserve a ticket because it is apparent that Macy Gray has a special place in each of our hearts. Her monstrous voice packaged with a calm spirit, is one that is captivating. I would love to revisit the years of life where existing was easier and nostalgic.
I absolutely LOVE Macy Gray ever since I was a little girl! I’d love to see her live in Portland.
Search an amazing unique voice..
Portland is lucky to get her
macy seems to have gained quite the following, and to know so many would be happy to witness her up close is a wonderful thing.
Neo-Soul!
I woudn’t say goodbye, choke, walk away or stumble if I won these tix 🙂
Oh yeah! One of the greatest debuts!
Yes! Macy!
Macy Wow!! Such a talent 👏 ✨ 😍
Would love to attend.. a powerhouse performance by Macy is what I need right now in My Life!
I love her voice, I have not had a chance to see her live after so many years, I would love to attend!
One of the only impressions I can do is Macy Gray. Be cool to win the tickets.
Saw her open for Bowie at the Wiltern. I was impressed! Would love to see her again.
my favorite part of spider-man (2002) is macy gray performing at the thanksgiving day parade
Still hoping to hear her someday
MacY graY on my BIRTHDAY 🎉
OMG! This would be a dream! SHe is a phenomenal singer with such a distinct voice. I would love to attend!
We are on holiday from the Netherlands and it would be an honour to watch the legendary Macy Gray