Takes place right after the events of The Million Dollar Tip (2014). Focuses on Will and how he is coping with the death of his best friend Evan, when all of the sudden his life is turned upside down once again by the mysterious Tip Man.
| Actor | Role |
|---|---|
| WWill HawkinsWill | Will |
| CCole BechererEvan | Evan |
| RRyan CardwellOne Face / Juan Phosay | One Face / Juan Phosay |
| JJulie GnadingerSam | Sam |
| LLandis HelwigLift King | Lift King |
| BBrad MiddletonOfficer Blake Delmar | Officer Blake Delmar |
| EEvan PrideBoss Morelo | Boss Morelo |
| SSydney MeyerDr. Till / Party-goer | Dr. Till / Party-goer |
| GGordon KellerGil (as Erik Moth) | Gil (as Erik Moth) |