by Gaines Entertainment Services - Thumbtack Top Pro!

5 (26)
Gaines Entertainment specializes in upscale event entertainment. We pay close attention to every detail from wire management to event attire.

In the past year we entertained family and friends at over 25 wedding receptions. Our modern DJ set ups and tasteful music choices are the core of this success!

Our school services have received rave reviews from UTSA, Brandeis High School, Brennan High School, Jefferson High School, MacArthur High School, Clark High School, Johnson High School, Stevens High School, Jay High School, and more. We give students a high energy dance with clean music, interactive emcees, music videos, bubble machines, UV lights, and club style light shows.

We enjoy making our clients feel special. It's not every day that you have a wedding reception or a large school dance. Knowing this. We strive to make every dream come true, whether it's matching your wedding colors to our lights or creating a custom monogram with your school name. Gaines Entertainment aims to please.
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Years in business


Times hired on Thumbtack


Number of employees


Background check



San Antonio, TX 78247
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Photos and videos

11 photos 29 { videos


Customers rate this pro highly for responsiveness, professionalism and value.
  • Ms. B.
    Wedding DJ
    I'll be booking him again!
    Jul 31, 2017 • Verified Review
  • Laura A.
    I truly believe the music makes any wedding reception and Winston did just that ours! Our dance floor was full the entire night! He was great throughout the whole planning process and of course during the actual reception! I would recommend him for any event!
    Jul 10, 2017
  • Kristina B.
    Gaines Entertainment Services DJ'd our inaugural Walk for Wishes for Make-A-Wish Central & South Texas. He did such an incredible job and was wonderful to work with. We will definitely be working with him again in the future!
    May 11, 2017
  • April M.
    Gaines Entertainment was extremely easy to work with! They go above and beyond to make sure that you have the best possible experience! Thank you!
    Apr 11, 2017
  • Daniel F.
    Excellent experience with Winston and his team for the second year in a row. Great energy and music that made this year's prom extra enjoyable for our students. We will definitely be working with Gaines Entertainment Services next year!
    Apr 10, 2017
  • Rudy R.
    He did a nice job even as it was a last minute event. Played the music we wanted to hear keeping the party going all night.
    Apr 3, 2017 • Verified Review
  • NASPA V.
    Fantastic experience. Thanks!
    Mar 16, 2017
  • Jonathan R.
    Gaines Entertainment Services was an absolute pleasure to work with. Our wedding day was an indoor/outdoor event with the dinner and dancing held outside. Due to un-predicted weather, we had to change the entire layout last minute. Winston and his team were phenomenal, and worked with our wedding planner to have the last minute changes flow perfectly. Our guests are still talking about how wonderful the event was, and how much fun it was to dance the night away. If you are looking for a top-notch high-quality DJ and lighting service, Gaines Entertainment Services is the best in San Antonio. Our wedding will be forever memorable and we couldn't have done it without Winston and Tory.
    Mar 11, 2017
  • Cynthia K.
    Great communication prior to event, professional and guests enjoyed him & music selections. Definitely would recommend and hire again!
    Feb 12, 2017 • Verified Review
  • Stephanie G.
    Wedding MC Services
    Hiring Gaines Entertainment was the best move we made for our wedding!! We hired him for DJ and lighting services and could not be happier. Winston was friendly, on time, affordable and made the event flow so smoothly!!' He had all guests up laughing and dancing the entire night. We also had a band play and he made the transition flawless when the band went on breaks! He was so nice and easy to work with and definitely was the icing on the cake for a wonderful wedding! If you are looking for someone to hire for your event I can't speak highly enough about Gaines Entertainment! You will Not be disappointed! Thank you again Winston!
    Jan 3, 2017 • Verified Review
  • Kim S.
    Winston was awesome at our company Christmas party from beginning to end! He was very personable and engaging with us as hosts and also with our guests. Music was very well coordinated with our theme and then varied at the end of the evening to accommodate guest's requests. Highly recommend DJ Gumby!!!
    Dec 18, 2016 • Verified Review
  • Sereena W.
    I was very pleased with the service provided. Gaines Entertainment (Winston and BJ) where very professional and fun. They were the POP to our 2016 Holiday Party. Thank you for your outstanding work. We look forward to using your company again in the future.
    Dec 13, 2016 • Verified Review
  • Cindy A.
    I highly recommend Gaines Entertainment Services! The services provided were excellent. The elite lightening, music and mc were beyond better than expected. Transitions of music and selection were just perfect! The DJ was very professional and funny! Everyone keeps complementing on a job well done. Definitely look forward in the near future to contracting Gaines Entertainment Service for upcoming events. Thank you once again for the services provided!!! Bride and groom were highly satisfied as well as their guests. ^_^
    Nov 22, 2016
  • Stephanie L.
    Winston did a great job! He was punctual and professional, and he was very easy to work with. He was more than willing to accommodate any requests, whether from the Bridal Party, the venue coordinator or the guests. Winston was quick to respond to any questions or concerns prior to the wedding day and he went out of his way to personalize the reception. Should I need a DJ in the future, Winston will definitely be my "go to" guy!
    Nov 14, 2016
  • Mica B.
    Amazing service. Mr. Gaines delivered a wonderful party atmosphere. Would absolutely recommend for any type of party :)!
    Nov 10, 2016
  • Paige B.
    My students loved you at the pep rally! We cant wait to have you back!:)
    Oct 21, 2016
  • Matt D.
    They were professional and courteous. We had specific musical needs and they not only met them, but went above and beyond for our pregame tailgate party!
    Sep 29, 2016 • Verified Review
  • Katie M.
    Very easy to work with and professional. The music selection and timing was perfect. I would definitely hire him again.
    Sep 29, 2016 • Verified Review
  • Bryan R.
    Incredible! Our DJ kept the dance floor full the entire night! He never missed a beat keeping all ages entertained and having a great time! When people say its the best party they have ever been to, you know the DJ was rocking the night! Thank you!
    Sep 19, 2016 • Verified Review
  • Tiffany M.
    Wedding DJ
    He did an amazing job was very professional I would definitely use him again he made my wedding day .... A day we will remenber forever. Thank you
    Aug 29, 2016 • Verified Review
  • Denise C.
    Dj Gumby was a big part in making our anniversary celebration a great success, he played all the music that was on our list and took requests. I would definitely hire he again. Thank you so much, it was a night to remember.
    Jun 12, 2016 • Verified Review
  • Lindy M.
    Awesome job! Arrived early and was ready to go when the kids arrived to their 8th grade celebration! Interacted with the kids, announced prizes, started dances, and kept the party going for 2 hours. The kids had such a great time! Thank you!!
    May 28, 2016 • Verified Review
  • Tammy G.
    Top 40 DJ
    He is an amazing D.J. Would definitely hire him again! He kept the teens entertained and I would hire him for an adult party as well!!
    May 23, 2016 • Verified Review
  • Carolina S.
    Apr 24, 2016 • Verified Review
  • Amy G.
    Top 40 DJ
    Winston Gaines (DJ Gumby) was exceptional. He showed up 45 minutes ahead of time to our house to set up, MC’ed the whole party including teaching two dances, judging dance competitions, and games like minute to win it and tp wrap. He brought glow stick bracelets and had a multicolor flood light and professional sound/DJ booth. It looked really cool. We sent him a playlist, and he honored it. He stayed afterwards to pack up his equipment and get feedback from us regarding the party. The middle schoolers really liked him and interacted with him. He also let the birthday girl make an announcement and be guest DJ for a song. She had the time of her life. He also remembered the names of the kids that he met, which made them feel really special. It is hard to get all 25 kids interested and engaged the whole time, and that is what DJ Gumby did, even with the shy ones. I think he would be ideal for any middle school or high school dance as well, and great for a sweet 16 or Quincenera. For the schools, he said what he likes to do is meet with the students ahead of time and get their feedback on what their vision is for the event. He has a ton of energy and is very charismatic and professional, humble as well. Highly recommend!
    Mar 1, 2016 • Verified Review
  • Andrea J.
    This experience was excellent from start to finish. He was very professional, timely and prepared. We hired this DJ for a house party for my 13y/o and about 15 friends. It was a relatively small party, but the kids had an AMAZING time. DJ Gumby kept the kids dancing and engaged the whole time, and played great (appropriate) music. He also made the birthday girl feel very special. My daughter said multiple times, "that was the best time I've ever had." I would definitely hire him again and I highly recommend him.
    Feb 27, 2016 • Verified Review
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What should the customer know about your pricing (e.g., discounts, fees)?
At Gaines Entertainment Services, clients are encouraged to pick a package from the company website. If you're unable to choose a package, we'll be glad to create one that fits your needs.
What is your typical process for working with a new customer?
We meet with new customers in person to discuss their needs. Every new customer is different, so we take this portion very seriously. We include (3) total meetings in our services. The first meeting lasts 30-45min (discussing expectations and event specifics). The second and third meetings are used to go over details. This usually includes additions/changes to floor plans, itineraries, and music.
What types of customers have you worked with?
Schools: University Of Texas - San Antonio, Northeast Lakeview College, Brandeis High School, Clark High School, Johnson High School, Brennan High School, Jefferson High School, Stevens High School, Marshall High School, White Middle School, Timberwood Park Elementary School, Krueger Middle School Non-Profit Organizations: For The Kids (UTSA), Big Brothers Big Sisters, Corporations: Pluckers Wing Bar, Medtronic, Baptist Health System Newlyweds (Ages 18-40)
What advice would you give a customer looking to hire a provider in your area of work?
PLEASE don't hire entertainment professionals based on price alone. "You get what you pay for." Contact the company that you're interested in. You can usually gather a lot based on how quickly and professionally the company answers you. Ask the DJ or production company for their insurance.
What questions should customers think through before talking to professionals about their project?
Do I need Lighting? Most people overlook the impact dance floor lighting can have on their event. Will I need an MC? A professional MC leads your event in a friendly way. This person starts the party and keeps things on schedule without coming off as pushy. Event Date/Time, Number of guests, and Budget.

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