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Weddings

Gaines Entertainment Services Reviews

Gaines Entertainment Services

Gaines Entertainment Services

San Antonio, TX
5.0 out of 5 rating, 43 reviews
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Reviews

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    Mckenzie Sent on 11/03/2025
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    10/10 the best DJs ever!

    I cannot recommend Gaines Entertainment enough! Stephen brought my reception dreams to life and turned it into one big party! He was so detailed, meticulous, thoughtful, energetic, and SO MUCH FUN! He listened to exactly the kind of music we did and did not want to play and kept the dance floor packed all night! He was so detailed in his planning process and made all aspects of our wedding day full of energy! I wanted our wedding to be memorable for how much fun everyone had and Stephen made it happen! 10/10 recommend Gaines Entertainment and DJ Ammunition!!!!
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    Sara Sent on 11/26/2022
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    So easy and so professional !

    We loved working the Gaines entertainment. It was very organized and it was so nice having a portal to see payments and keep your music and timeline all together and clear. Louie was our DJ and he was so easy to work with and always responsive and available for questions and making our personalizes happen. Really wonderful experience and made our wedding day so fun. Highly recommend
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    Patricia Sent on 11/08/2022
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    The most fun!

    We were worried about having a DJ at our small wedding (around 50 people) and there just being an empty dance floor. Mr. Gaines was a total hype man at our wedding! Honestly the most fun I've had on the dance floor in a while. He tried to get in all the songs we requested and smoothed the 80's and Latin vibe we had in our mixed wedding. We have no problem recommending his services. A+
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    Robert Sent on 12/13/2021
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    Amazing job

    We used Gaines entertainment to dj our wedding and honestly they did a superb job. Louie was very positive and energetic. He helped us in any way we needed .The music selection kept our event lively and our dance floor was never empty. I would recommend Gaines entertainment 120% if I hire a dj for any future events it will be with Gaines. They truly set the bar when it comes to Dj’s. I would like to thank them for an unforgettable night.
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    Brittany Sent on 11/18/2021
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    A pleasure to work with!

    Winston was amazing! He helped us decide how we wanted the night to flow and played a great variety of music that ensured everyone was out on the dance floor. He was so professional and even made sure we took the time to have our last dance when things got hectic towards the end of the night. His pricing was a little higher than some of the other DJs we looked at, but was absolutely worth it. Do not let that stop you from working with him and his team – they are truly the best!
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    Katherine Sent on 08/15/2021
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    Amazing Service!

    We had a great experience with Gaines Entertainment! Winston was very responsive and helpful in our communication leading up to the event. I appreciated how organized their client portal is- helps make planning easy. And they did a fantastic job during the event itself! Stephen was fun, professional, and kept the dance floor going strong the whole night. He did a good job of getting a feel for our crowd. Would absolutely recommend!
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    Kelsey Sent on 12/05/2020
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    Best. Dj. Ever.

    YALL! If you’re looking for an amazing DJ, look no further! I truly cannot recommend them enough! DJ Gumby (Winston) was PHENOMENAL! He read the crowd & played the music he knew would get our families out on the dance floor. We got at least 20 compliments on our DJ from friends & family. Their customer service is top notch, when they found out we were one of the couple devastated by the Noah’s closure they went above & beyond what they remotely had to. I 100% recommend them (& their indoor safe sparklers)!
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    Lindsey Sent on 10/15/2020
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    Best DJ Around

    Hands down the best dj, we had an absolute blast with DJ Gumby! He knew exactly how to get the party started and keep it going! Would highly recommend for your wedding and the photo booth is awesome!!!
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    John Sent on 05/03/2020
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    Amazing Wedding DJ!

    Winston was an amazing wedding DJ. He helped us plan every detail from our entrance, to the first dance, to the garter toss, and executed them perfectly. His sound quality and music selection were excellent and the up lighting setup perfectly set the mood for an amazing evening. He's also really fun and energetic, and easy to work with, which is a plus when you're stressed out and rushing around on your big day. We had a lot of people tell us after the wedding that the DJ was so fun and helped make the evening even more memorable.
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    Jacquelyn Sent on 04/08/2020
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    Perfect Playlist

    Gaines Entertainment was amazing. Winston was checking in with us throughout our planning. He provided helpful insight to creating a great wedding environment. He was professional at all times and kept my wedding fun and exciting. Definitely had a great time and enjoyed the music!
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    Kristine Sent on 03/25/2020
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    So much fun!

    Winston and his crew truly made my reception so much FUN!!! They kept the party going and the dance floor full all night! Thank you Gaines Entertainment for making it so much fun!!!
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    Vanessa Sent on 03/19/2020
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    Louie was excellent!

    We hired Gaines entertainment and spoke to Winston about our wedding dreams and what music we would like played. He recommended DJ Louie who did an amazing job! We are still getting compliments about how that was the best music our guests have heard at a wedding. Even the other vendors, who have attended hundreds of weddings, raved about it. Thank you Louie and Gaines Entertainment for an amazing day!!
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    Ileana Sent on 02/20/2020
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    Amazing DJ

    DJ Gumby was so much fun! He was very detailed with every single step of the reception! He would quickly respond to our emails/messages and he would feel out the crowd to see what kind of music to keep playing! All of my guests loved him and said they had so much fun hands down.
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    Jericho Sent on 01/12/2020
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    Best DJ around

    Winston did an awesome job! More than helpful up to the last minutes before making our grand entrance! We Could not leave the dance floor
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    Kasheen Sent on 01/10/2020
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    a.m.a. z.i.n.g

    I would recommend these guys for any and all events. They're passionate about what they do and are very professional. They understand music and know how to read a crowd and play just the right type of music to get any and everybody moving on the dance floor.
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    Devyn Sent on 10/12/2019
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    AMAZING!! Highly Recommend

    Gaines Entertainment reached out to us last minute to see if we wanted an indoor sparkler fountain during our first dance. Needless to say, it was beyond AMAZING! We kept it a secret from our guests which made it even more awesome! Highly recommend!!!
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    Jamie Sent on 10/03/2019
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    LOVED - Sparklers for First Dance

    We absolutely LOVED the sparklers in our wedding.
    It made our first dance so special.
    They did a wonderful job.
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    Ali T. Sent on 07/25/2019
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    So. Much. Fun.

    From start to finish, working with Winston was AWESOME. He was so easy to work with, was quick to answer questions and even had helpful suggestions when we weren't sure how the evening should flow. Not to mention, the dance floor was packed all night. Our guests were a mix of young and old, he played something for everyone which is tough to do! We are still getting compliments on how fun the wedding was. He is without a doubt the best.
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    Keely Sent on 07/08/2019
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    Reyna Wedding

    Winston was hired by one of our clients to DJ their wedding ceremony/reception. From a coordinators perspective we felt that he communicated well with us and our client, was very accommodating, upbeat, and read/responded to the crowd well. HEHC would recommend Winston to future clients.
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    Johnathan Sent on 07/02/2019
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    The DJ you deserve for your wedding!

    Winston was probably the best addition to our wedding. He easily understood what we wanted and expected from a DJ. He made the process extremely easy and keeping in contact was punctual. He sent made sure we were on tract with everything else that we needed done for our wedding with his email reminders and though we were out of town for the entire process he made it easy on us to get our DJ questions answered with he face-time consultation. He was excited as much as we were! He asked the general vibe we wanted and he took care of the rest. He played the right tunes and was our personal hype man. He kept the life of the party going through out our wedding, his signature photos make it even better. I recommend him to anyone planning a wedding. He’s the best professional in town!
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    Anna Sent on 06/13/2018
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    Our reception was awesome thanks to Gaines Entertainment. We wanted a fun reception, and they made it happen! So many of our friends and family were on the dance floor, even people we didn’t expect. DJ Gumby made the dance floor so welcoming and fun without it being forced. Could not have asked for a better DJ. We wish the night didn’t have to end!!!
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    Angela Sent on 05/28/2018
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    Winston is incredible! We stayed in touch with the planning of my wedding over 6 months, he was always responsive, had great ideas, he met all my requests and more. I wanted to walk down the aisle to a song from my husband's favorite movie, not only did he find it, but he edited it down from 5 minutes to 1 1/2, making sure to include the climax of the song. It had all my guests in tears. He checked on me the entire night, always asking how I was and what I needed. My guests loved him! He was hilarious! Not to mention professional, current, & appropriate. My guests LOVED the photo booth he supplied. He kept us all entertained, every minute of the evening, the dance floor was packed, he made our wedding a celebration of a lifetime!
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    Caitlyn Sent on 03/15/2018
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    We found Winston at a wedding fair and the way he was communicating and answering questions from people immediately made him stand out from all the other DJ's there. We were concerned about spending so much of our wedding budget on the entertainment, but I can safely say my wedding would not have been the same without him. From the second he showed up (right on time btw) he was focused on not only getting himself ready, but getting me whatever I needed as well - including drinks once they started being served. He had a time line of the event and he was communicating with my maid of honor and photographer all night and as a result we ended up being ahead of schedule. He also managed to get almost every person on the dance floor by the end of the night. He definitely didn't just sit there and click a button to make the next song play. He was super interactive without being over the top. I honestly can't say enough good things about this dude. Just book him and save yourself the time and energy worrying about all your other entertainment options.
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    Kristi Sent on 03/10/2018
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    Gaines entertainment services was super flexible and very helpful in planning our wedding. They played great music and did a great job on getting the crowd excited! Would definitely recommend!!!
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    Chelsea Sent on 03/05/2018
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    Gaines Entertainment made our wedding so special! All of my guest loved him and I continued to receive complements throughout the night! Winston was great at interacting with my guest and our wedding party, I know our wedding wouldn’t have been the same without him.
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    Samantha Sent on 01/17/2018
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    Im so glad my husband found Gaines Entertainment Services at Bridal Extravaganza at the Marriott. Winston has been great working with us, my in-laws and wedding coordinator to ensure our day was perfect. There was never a doubt in my mind from first speaking with him that the music and entertainment would be nothing less than great. Winston was punctual with meeting with us after the holiday due to us planning an out of state wedding in our hometown San Antonio. He also has an easy, accessible website to create your event and playlist of music. Our wedding party was very diverse and he ensured everyone had a moment to shine. Winston was willing to work with our band for our second line dance and even stepped in early to get the reception started after dinner. Winston provided services for our ceremony, cocktail hour, and reception. I would recommend his services to anyone who is looking to having a stress free and entertained Wedding or event.
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    Allison Sent on 12/10/2017
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    Winston is the best DJ ever! He truly went above and beyond at our wedding, helping out with much more than just his responsibilities as our DJ. He was incredibly professional, outgoing, and had great communication with us from the beginning. All the music was exactly as we had imagined from the ceremony to the send off. All our guests had an awesome time on the dance floor! We truly appreciate all Winston did for us and would absolutely recommend him, as he did a exceptional job at our wedding!
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    Jennifer Sent on 12/04/2017
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    We have used Winston's DJ services for our Homecoming Dance for the past three years. He knows how to get the students out on the dance floor and have a great and safe time. We started with having 700 kids come to the dance, but since having Winston as DJ we now have 1000 + kids coming. We will continue to have him DJ this dance. He has done our proms and food fests as well. You will have a great time at your event with Gaines Entertainment Services!
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    Taylour Sent on 11/30/2017
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    Super great experience with Winston, he really made our wedding something special and was very accommodating!
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    Emily Sent on 11/20/2017
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    Winston was amazing! He met with my husband and I over coffee to go over all of the details beforehand, he showed up extra early to the venue, and he stayed in constant contact with the venue coordinator, the photographer, and the caterer. He even made sure that we had plates of food ready at our table after we made our grand entrance! He played the songs that we wanted and took all of our friends and families' requests. He was also very flexible when we decided to move the venue inside at the last minute due to weather. Would definitely recommend!!
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    Jabari Sent on 10/04/2017
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    If your looking for a great DJ that will keep the dance floor full be sure to go with Gaines entertainment services. After our wedding many of our guest couldn't wait to tell us how much fun they had, a large part due to our DJ. Thanks again!!
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    Ashley Sent on 09/29/2017
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    Winston is very professional and responsive. The quality of his work is supreme! His equipment is high end and sound quality is fantastic. If you need a DJ that knows their stuff Winston with Gaines Entertainment Services is the best choice!
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    Jonathan Sent on 09/29/2017
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    Gaines Entertainment definitely made our wedding very memorable. My spouse and I never left the dance floor and neither did any of our guests. People still talk about how fun everything was to this day. If you are looking for professionalism at it's best, Winston is your go-to DJ. He worked very closely with our wedding planner and even helped with lighting and layout of our event space. Unfortunately we had to have very last minute changes in our outdoor wedding due to rain, however Winston was very reactive and helpful on coming up with plan B. I would definitely recommend on stopping your search for the perfect DJ and go with Winston at Gaines Entertainment Services. Why would you want your night to be awkward with no one on the dance floor when Winston if the perfect hype-man for the job. With Gaines Entertainment Services, you get more than just a guy playing music.
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    Amy Sent on 09/29/2017
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    We have used this DJ for two birthday events. He shows up on time, set up very well, has some amazing lighting, cleans up when he is done, and is well groomed and good looking. He is very professional, and he knows how to engage a crowd of any age and get them dancing. I highly recommend Gaines Entertainment and will use them again!
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    Molly Sent on 09/29/2017
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    Winston was great to work with! All communication was clear and easy to get a hold of him. UTSA Students enjoy his entertainment as well. I will definitely work with his DJ services again in the future.
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    Sereena Sent on 09/28/2017
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    Winston Gaines and his team with Gains Entertainment provided the best experience during our 2016 Holiday Party for KRTC. The booking process was easy to do and complete. The packages and prices Gains Entertainment offer are fairly reasonable. Winston and his team made sure everyone at the party was having a good time. During our raffles, Gains Entertainment took over. Called each ticket selected and announced the winner. They played all the different types of music requested and kept the music flowing from one type to the next. I recommend Gains Entertainment for your next Wedding, Holiday Party or even your next bbq backyard party.
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    Michelle Sent on 09/28/2017
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    I saw Winston Gaines at a wedding fair and loved his personality. He's very outgoing and polite and knows how to get a crowd going. His website is very easy to navigate and has a lot of good information on it. I selected all the songs I wanted playing at the wedding and reception from his website lists (if the songs not on there, which it more that likely will be, he'll get it for you). The website gave me helpful tips like what were popular songs to play during the bride/groom, father/daughter, mother/son, etc dances. And the site lets you pick your timeline from start to finish along with what songs you want played during each step of the way (this broke it down and made the wedding day way less stressful). During our reception my best friend descided last minute she wanted music played at a certain point in her toast, and with only a minute notice Winston had it done. He was also very good at determining when to play what music in order to get all of the guests dancing (we had 20year olds to 90year olds and they all ended up on the dance floor). Overall Gaines entertainment is a great company and I recommend their services to whoever needs a dj.
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    Windi Sent on 09/28/2017
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    We absolutely loved DJ Gumby. He's become sort of a fixture now with our group of girls, and their friends. He DJ'd a friends birthday party, then we used him for our daughters birthday. Even the neighbors came to see what all the fun was! Winston was super friendly, extremely fun and just all around great to the girls. He pays great attention to detail, such as timing. On his own, he keeps the time table on schedule. Such as the cake, certain dance/song games, and a fun fashion show (it was halloween). He even knew when to play music for the mom's when the girls were having downtime (or eating cake). He was hilarious with a group of boys that "crashed" the teen girls b-day party! Definitely has that "intuitive fun" personality you want in a DJ with a bunch of teens. I recommend him all the time! Great guy, great fun for all of us.
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    Am Sent on 09/28/2017
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    I have used the DJ services from Gaines Entertainment multiple times. They are a very reliable company. They are consistently on time and attentive to requests made to them. They are professional and easy to work with.
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    Lauren Sent on 09/28/2017
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    Gaines Entertainment is the absolute BEST there is! We have been using the DJ services for our corporate events for years now. Winston has DJ'd holiday parties, product launches, fundraisers, and more. We've also done karaoke on site. Our team always gets excited when we share that DJ Gumby is coming to the building! Beyond the corporate events, many of our employees have hired him for their personal Weddings, parties, and more. He is very professional and knows how to hype a crowd. Zero hesitations; you will not be disappointed!
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    Krystal Sent on 09/27/2017
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    Gaines Entertainment provided an unforgettable experience. DJ Gumby was very professional and easy to work with. He took the time to listen to my request and followed up with feedback and suggestions about flow. He listened carefully and was flexible, fluid and calm. He is funny and charming and goes the extra mile to provide the best customer service. I would highly recommend Gaines Entertainment.
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    User2921427 Sent on 12/21/2016
    5 out of 5 rating
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    Winston has been absolutely phenomenal to work with from beginning to end! I saw him at a wedding I was in last year and KNEW he would be the dj for my wedding. His website was easy to navigate through and he had various payment options fit for any budget. Highly recommend!!
  • Michelle
    Michelle Sent on 07/06/2019
    4.8 out of 5 rating
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    Disney in July

    Overall, fantastic experience! There was some confusion with the timeline but we really enjoyed the mash up/transitions from country to reggaeton and then back to country. It was done really well. Especially the final dance at the end of the night after everyone left. That was the cherry on top for us! Definitely would recommend him to anyone looking for a funny, hype, down to earth DJ. Thank you for being a part of our most memorable night!
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