This DLC was released as a pre-order bonus for those pre-ordering the console versions of Sonic Generations at GameStop. Casino Night soon after became available for those who downloaded the Steam version of Sonic Generations on December 26, 2011, and could originally be purchased for USD $1.59, GBP £0.99, EUR €1.59 or AUD $2.99. As of September 29, 2016, this DLC has become available for free to all Steam owners. Also, as of April 2018, it has become a free download on Xbox Live after Sonic Generations was added to the Xbox One backwards compatibility list.
Casino Night is set during the night in a city filled with neon lights and casino-themed buildings. Most of the Stage takes place on a large-scale pinball table on which Sonic is the size of a pinball. This table is mostly blue and is covered in various red and yellow symbols and imagery based on the signature art style for Sonic Generations. The middle of the pinball table in particular shows an image of Classic and Modern Sonic with the "SONIC GENERATIONS" logo below them and the seven Chaos Emeralds above them. The pinball table also features various types of Bumpers and even Dash Panels, Springs and Dash Rings.
On both sides of the pinball tables are signs that says "SONIC" and "MILES" respectively, as well as artificial palm trees. Also, on the left side of the pinball table (and above it as well) is a golden statue of Tails. In addition, on the building in front of the pinball table, there are extra pinball courses that the player can reach, and a neon sign on top of it that says "Casino". Lastly, in the uppermost left area is a giant vending machine/slot machine with a glass bowl filled with Rings.
In Casino Night, the player's objective is to get the highest score they can get (the maximum being 999,999 points) by using either Classic Sonic or Modern Sonic as a pinball. By shooting Sonic up ramps and into targets, the player can reach a slot machine where the Jackpot Medals collected on the table can be used to play. Matching three symbols on the slot machine will make Rings rain down on the pinball table, thereby increasing the player's score. The more Jackpot Medals the player collects, the easier it will be to get a Jackpot on the slot machine.
On the pinball table, the player can launch Sonic using /. The player can also control the Flippers using or / or /[Q] or [E] respectively. The pinball table can also be titled using the Left Stick, although using this function repeatedly will eventually lock up the controls until Sonic rolls off the bottom of the pinball table.
In addition to the aforementioned controls, the player can also use a special ability with / that depends on which Sonic the player is using; Modern Sonic gets a Boost which can be used until the Boost Gauge runs out, while Classic Sonic is given three Spin Dashes to change direction with.
The Stage will last until Sonic has rolled off the pinball table a total of three times.