Use this to generate a smalldatetime between 01 Jan 1900 and 06 Jun 2079 (not checked, SQL not installed)
DATEADD(day, (ABS(CHECKSUM(NEWID())) % 65530), 0)
NEWID is better then trying to use RAND: RAND does not generate different values row in a single SELECT or UPDATE (well it didn't in SQL 2000, in case behaviour has changed).
Edit: like this
UPDATE
table
SET
datetimecol = DATEADD(day, (ABS(CHECKSUM(NEWID())) % 65530), 0)
Edit: changed 65535 to 65530 and added ABS to avoid overflow at upper limit of range
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