Anda dapat melakukannya dengan agregasi bersyarat dan fungsionalitas jendela/analitik:
SELECT *,CASE WHEN [Date] < MIN(CASE WHEN FilmName = 'Gladiator'
THEN [Date]
END) OVER(PARTITION BY Cust_Nr)
THEN 1
ELSE 0
END AS Before_Gladiator
FROM Table1
Demo:SQL Fiddle