Playing opposite nerdy sitcom icon Urkel (Jaleel White) on "Family Matters" was often a thankless task for the young actor, but he managed to hold his own on screen, remaining with the series through its network switch to the end of its run. Though he gained his greatest notice on the comedy series, McCrary already had notable credits before joining the series, including a pivotal supporting role as a terrorized black child in the acclaimed historical drama "Mississippi Burning" (1988). As "Family Matters" finished its TV run, he began to branch out into more challenging territory, even playing boxing legend Muhammad Ali in the 1997 HBO biopic "Don King: Only in America".
McCrary returned to series television in the fall of 2000, playing a freedom fighter in America's oppressed near future on the UPN drama "Freedom". Riding an upward career trajectory, he also acted in the black comedy "Fifteen Minutes" and the comedy-drama "Kingdom Come" (both 2001). In the former, he was featured alongside Robert De Niro and Edward Burns while in the latter, set at a funeral, he co-starred Whoopi Goldberg and LL Cool J.