Short Bio

Sunny Side is a jazz band based out of New Orleans, Louisiana. They are heavily influenced by the music of Louis Armstrong, Duke Ellington, Nat King Cole, Fats Waller, and many other early jazz legends.

Sunny Side provides a full New Orleans style jazz band experience with 3 part harmonies, a solid rhythm section, and an energetic vocalist and dancer. 

During the 2020/2021 quarantine, Sunny Side provided a ‘Jazz in Coliseum Square Park’ series in the Lower Garden District of New Orleans hosting a variety of live music including themselves. Many locals expressed much gratitude for the music during the challenging time.

In May of 2023 they released their 2nd Album and first studio album “The Felicity Sessions” promoting this on their 2023 national tour.

In 2024 Sunny Side is planning their fourth national tour stopping in cities and towns between New Orleans, New York, and Ohio focusing on large swing dance events and jazz listening rooms across these states.

Sunny Side has also been playing regularly for private events and weddings since January of 2020.  In 2021 and 2023 Sunny Side won a “Best of Weddings” award going to the top 5% of wedding bands on

Live Videos



“My wife and I were fortunate to have SunnySide perform at our small, intimate wedding at Race & Religious in New Orleans. Throughout the entire process, our main point of contact was Rob. He was exceptional in every aspect, making the whole setup process a breeze. Rob was highly responsive to our phone calls and emails. He asked insightful questions, ensuring all the necessary details were covered for a seamless day, particularly concerning the second line and wedding performance. A notable instance showcasing Rob’s exceptional service happened when the band arrived at our wedding. Heavy rain had persisted for nearly an hour earlier in the day, and ominous clouds lingered around our event location. Rob asked, “Do you have a backup plan in case it rains again?” Unfortunately, we didn’t. Without hesitation, he suggested, “If it’s okay, I have a tarp available, and we can cover the band if it rains.” Fortunately, it never rained again, but we are immensely grateful for Rob’s forward-thinking approach. He also set up the route and took care of our permits for the second line; this was very helpful as we’re from Wisconsin, saving us time from navigating these issues. As for the performance, SunnySide truly rocked it! The second line experience left our families in awe, and their infectious energy set the perfect tone for the entire night. We must also mention Darold, the lead vocalist, in this review. He did an incredible job of singing, and his dance moves will leave you speechless. We decided to have our wedding in New Orleans for two reasons: the food and the music. Thanks to SunnySide, our event was spectacular – showcasing the best of New Orleans jazz music.”

  • Joshua B. Wedding Wedding Review

“The service provided by Sunnyside Jazz is truly exceptional. From start to finish, their professionalism shines through, making the entire experience seamless and enjoyable. Their attention to detail ensures that every aspect of their performance is executed flawlessly, leaving no room for disappointment. The communication with their team is prompt and courteous, making it easy to coordinate and plan events. Overall, Sunnyside Jazz delivers a top-notch service that exceeds expectations and leaves a lasting impression.”

  • Katy C Wedding Review

“We hired Sunny Side to play at a welcome party the evening before our son’s wedding. The band far exceeded our expectations. Rob and the band captured the exact New Orleans vibe we were looking for and set the mood for warm and relaxing evening. Guests were telling us how wonderful the band was all weekend long. Rob was a pleasure to work with and we felt the cost was extremely reasonable. Sunny Side was the perfect choice and we would highly recommend them to everyone.”

  • Julie P Wedding Review

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Management and Booking

Rob Montgomery