In SQL Server 2008, a new insert feature is available which will make inserting of values easier. 

How do you insert multiple rows in SQL with using only one SELECT statement:

SQL Server 2008 Method of Row Construction:
INSERT INTO MyTable (FirstCol, SecondCol)
VALUES ('First',1),
('Second',2),
('Third',3),
('Fourth',4),
('Fifth',5)

Previous method 1:
INSERT INTO MyTable (FirstCol, SecondCol)
VALUES ('First',1);
INSERT INTO MyTable (FirstCol, SecondCol)
VALUES ('Second',2);
INSERT INTO MyTable (FirstCol, SecondCol)
VALUES ('Third',3);
INSERT INTO MyTable (FirstCol, SecondCol)
VALUES ('Fourth',4);
INSERT INTO MyTable (FirstCol, SecondCol)
VALUES ('Fifth',5);
GO

Previous method 2:
INSERT INTO MyTable (FirstCol, SecondCol)
SELECT 'First' ,1
UNION ALL
SELECT 'Second' ,2
UNION ALL
SELECT 'Third' ,3
UNION ALL
SELECT 'Fourth' ,4
UNION ALL
SELECT 'Fifth' ,5
GO

Using SQL Server 2000, no problem.  Get a test db on SQL Server 2008 – do your updates – then use a tool to script out the inserts.  I use SSMS Tools Pack: http://www.ssmstoolspack.com/