Liverpool striker Sturridge and Aston Villa defender Richards were in the big apple with friends on an end of season trip when they ran into Stiller at a bar.
The 51-year-old star of comedy hits Dodgeball, Zoolander and Tropic Thunder posed for photos with the Premier League striker and his entourage.
Shouts to @benstiller top man. My team @micahrichards @flash_richards @marshman1989 @dreamville_ar and my bro Leon. Much love you !! ❤#NYC A post shared by Daniel Sturridge - Dstudge (@iamdanielsturridge) on May 31, 2017 at 10:31am PDT
After struggling with injury this season, playing in only seven games for Jurgen Klopp's Reds, Sturridge will hope his time away from the game is the perfect elixir to regain his health and best form ahead of next season.
Sturridge wasn't the only one enjoying their offseason break as Feyenoord's Aussie shotstopper Brad Jones put being overlooked for the Socceroos World Cup qualifier and Confederations Cup squad behind him as he enjoyed a family holiday in Dubai with his wife and kids.
Dubai was a popular spot for football stars with West Ham marksman Andy Carroll and Manchester United attacker Jesse Lingard also enjoying the warm temperatures of the Gulf Nation.
Lingard took time to feed a baby Tiger, while Carroll went swimming with Dolphins
Chelsea great John Terry enjoyed the sun and sand of Portugal after ending his Chelsea career with a Premier League title win.
Fresh from winning the FA Cup, Arsenal star Alexis Sanchez took his instagram famous dogs Atom and Huber on a boat trip in Spain as he takes time off away from football. It will be much needed respite for Sanchez with Manchester City, Chelsea and Bayern Munich all clambering for the Chilean's signature with his Gunners future in doubt.