Jay z ft sterling simms dig a hole
I think you may be thinking of a different song!
The song "Dig a Hole" is actually by Jay-Z, but it's a solo track, not a collaboration with Sterling Simms. The song was released in 2001 on Jay-Z's album "The Blueprint".
Sterling Simms is an American R&B singer-songwriter, but I couldn't find any evidence of him collaborating with Jay-Z on a song called "Dig a Hole".
If you're thinking of a different song, please let me know and I can try to help you identify it!