Jugar de vivo is an idiomatic expression that is used frequently in Costa Rica. Pasarse de listo is a synonym and is heard more in other Latin American countries. So what do these two phrases mean? Basically, “to be too smart for one’s own good.” They can also be translated as shrewd, clever, cunning, astute, a know-it-all or to be a smartass.
Un juega de vivo is a person who is a smartass or very sly.
All of us know people who fit perfectly into this category. The person who runs a red light or stop sign or someone who tries to outsmart the system by cutting corners are vivazos. A know-it-all foreigner is another example. By the way, sabelotodo is a know-it-all in Spanish.
Here is an example using this phrase. Antonio juega de vivo or Antonio se pasa de listo. Anthony tries to be too smart for his own good.
Here is a tico joke. ¿Qué hace un muerto en el Parque Central a media noche? ¿Te das (You give up?)? La respuesta: Está jugando de vivo. Je, je ,je