One of the best "free" entertainment offers to be found that I recommend is Bob Jackson, known as the piano man in the Rivers Roost Lounge at Port Orleans. I believe he entertains there Wed-Sun(call to confirm) from 8PM - Midnight. I say free, but you'll probably end up ordering a drink or two -you could go for a light dinner for that matter and combine your "free" entertainment with something to eat. This is a great time whether you go as a family or just as a couple. The person who wrote the following says it best:
Around 8, we got ready to go and headed over to the River Roost, which is Port Orleans' cocktail lounge. We were fortunate enough to be able to grab one of the last tables and settled in. We found a menu on the table listing the various signature cocktails as well as mentioned that we could order appetizers from Boatwright's. We started off with some soft drinks and an order of Nachos Supreme. Disney lounges are friendly to those that don't want to drink. They will give you no grief over ordering just a soft drink, in fact they will give you free refills on the soft drink.
Entertainment in the River Roost is provided by a comic piano player that goes by the name of Bob Jackson. His show consists of mostly pop standards, tv theme songs, campfire songs and the like. In other words it 'sall songs you have probably heard before and are familiar with. This is good because Bob's show is heavy on audience participation. There are two motto's "No one has more fun than us!", followed closely by "You will never see any of these people again" I know you might think this sounds cheesy or campy, but from what I saw everybody gets involved in the show. This is mostly because a lot of the songs have either obvious auidence parts or Bob makes up an audience part. If you are thinking you'll just sit back, wrong. I dont know how else to describe it, but Bob's enthusiasm is infectious and before you know it you too will be jumping up and down, waving your hands in the air and yelling (or singing like Edith Bunker) in your loudest voice stuff like "Have some Fun Tonight" in the cocktail lounge of a rather upscale looking hotel lobby. And if you hear a bugle call, well by the end of the evening you will instincitvely jump up and do your best Tarzan imitation.
Pay close attention to Bob's piano, becuase it is also a part of the show. This black upright piano gets so excited that when they say Bob rocks that piano, the piano literally rocks back and forth. Then you have bob himself who is a very personable entertainer who welcomes newcomers to the lounge between shows. He ask them were they are from, and gee whiz, Bob just happens to also be from whatever city they name, and a little while everybody else claims to be from whatever city the new arrivals are from. Bob takes two breaks but never leaves the lounge, instead spending his break time signing autographs and making his way around the room stopping to chat at just about every table. Oh, and for those that drink, be careful, Bob loves to haul out a song titlled Sara towards the end of the night. Its a perfectly innocent song, but its lyrics are a tounge twister when taken slow and sober, let alone when taken fast and with a few drinks. Just try keeping "Sarah, Sarah, sitting in a shoe shine shop, sarah sarah, sitting in a shoe shine shop, all day long she sits and shines, all night long she shines and sits, Sarah Sarah sitting in a shoe shine shop." straight.
All in all it was a great evening. After the show ended it was time to make our way back to the room. We got just about all packed up before going to bed, then told Stitch to take his own sweet time in waking us up tommorow. Sadly, tommorow is departure day.
We planned on watching one set, and wound up staying from 8:30 clear through last call, which at the River Roost is at midnight.