The Fun You Didn’t Know Was Waiting at Port Orleans Riverside
There are some Disney experiences you plan months in advance, dining reservations, Genie+ strategies, must do attractions. And then there are the moments that simply just happen, the ones that become unforgettable because you weren’t looking for them at all.
We had walked past Yehaa Bob Jackson plenty of times before, catching bits of music and laughter drifting through the lobby at Port Orleans Riverside. But it wasn’t until after the Disney Nerds Half Samplethon meet-up in November that we finally stopped and joined the fun. A group of us decided the night didn’t need to end just yet, so we headed over to Riverside together, ready for more laughs and a little extra Disney magic.
What we found wasn’t a headliner attraction or a heavily advertised show, it was something better. Yehaa Bob’s performance felt like one of those hidden Disney gems you only discover if you slow down, wander into a resort, and say yes to the moment. The show was lively, interactive, and full of joy, with Bob pulling the crowd right into the fun. Before we knew it, we were singing along, laughing, and feeling like we were part of something special!
We eased into the experience at first, grabbing seats toward the back of the room just off the lobby, happy to take it all in. We got there just before the first show wrapped up. Once tables began to clear, we made our move and suddenly found ourselves right up front, our whole Disney Nerd crew gathered together with snacks, drinks, and great big smiles. Yehaa Bob performs two sets each night, an earlier, family friendly show packed with beloved Disney tunes, including crowd pleasers like Toy Story’s “You’ve Got a Friend in Me” and Aladdin’s “Never Had a Friend Like Me”, followed by a later set that leans into a slightly more grown-up vibe. Somewhere in between came a rousing, hands in the air rendition of “Sweet Caroline”, with the entire room singing at the top of their lungs.
Bob’s show is equal parts comedy, music, and pure audience interaction, and that’s what makes it so memorable. He chats effortlessly with the crowd, somehow remembering little details and weaving them back into his songs and jokes throughout the night. Our Disney Nerd group quickly became part of the fun, belting out lyrics, clapping along, and fully embracing the crowd interactivity, with plenty of playful shout-outs along the way. My husband and I even earned a few mentions as his new friends from Canada. Between the laughter, the sing alongs, and plenty of toasts to friendship, it turned into one of our favorite nights of our trip, and one we’re already hoping to repeat.
In addition to the shows, Bob is also available for meet and greets between sets and after the performances. Guests can take pictures, chat with him, and even get personalized photos as a keepsake from the night. It’s a wonderful way to make the evening even more memorable and bring home a tangible reminder of all the laughs, music, and fun shared at the River Roost.
After long park days filled with crowds, wait times, and miles of walking, experiences like this are a reminder that some of the best Disney magic happens when you step away from the attractions and slow the pace just a little. Yehaa Bob’s show isn’t about racing to the next ride or checking something off a list, it’s about laughter, connection, and letting the day end on a high note. Staying up late or hopping over to a resort might feel like a small extra effort, but nights like this are exactly what make a Disney trip feel balanced, joyful, and memorable in a whole different way.
If you’re hoping to catch Yehaa Bob for yourself, you’ll find him at the River Roost Lounge inside Disney’s Port Orleans Riverside Resort. The resort is easy to reach by bus, boat from Disney Springs, or a relaxing evening stroll if you’re already nearby. Bob typically performs two sets each night, making it easy to fit into your plans whether you’re looking for family friendly fun earlier in the evening or a livelier, late night way to unwind. It’s the kind of experience you won’t see listed as a must do attraction, but once you know where to look, it’s a Disney gem you’ll want to return to again and again.
Moments like an evening with Yehaa Bob are exactly what make Disney feel endlessly magical. They remind you that the best memories aren’t always found on the most famous rides or in the biggest crowds, but in the laughter, the music, and the friends you share it with. Whether you’re a longtime Disney fan or discovering the parks for the first time, taking a little detour to explore the resorts can lead to some of the most unforgettable experiences of your trip, nights filled with music, smiles, and unexpected joy.
Just Keep Dreaming and Disney(ing)!
Terri Lee