Childress played collegiately at Wake Forest University, where he averaged 18.4 points per game for his four-year career.

In the finals, against a UNC team featuring Jerry Stackhouse and Rasheed Wallace, Childress scored 37 with 7 assists and hit a game-winning jumper with 4 seconds left in overtime.

Childress played in two NBA seasons for the Pistons and Portland Trail Blazers, averaging 2.4 points per game.

After leaving the NBA, Childress played in 1997–1999 in the Turkish Basketball League for Tofaş SAS and Konya Kombassan.

[3] Childress went on to play ten games for the Sydney Kings in the 2000–01 Australian National Basketball League season.