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Read the history of the band:

10 songs you probably know:
 

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20 songs you need to know: 
(obviously just a matter of opinion)
 
All Along the Watchtower (Bob Dylan cover)

How about a few stories?
 
Dave Matthews Band - the reason for the name
The most common reason is that the band, moments away from taking the stage for the first time, had not come up with anything yet, so they decided to go with the Dave Matthews Band until a better name was suggested.  There were no suggestions.
 
#34/#36/#40/#41 - the reason for the numbers as names
Dave Matthews has always numbered his songs as he has written them.  For these four songs, a creative name was never thought of, so they were titled using this number.  The lyrics to  I'll Back You Up are thought to make it song #1.
 
The Lillywhite Sessions - the story behind their failure
The Dave Matthews Band recorded these 12 songs in the spring of 2000 for an album that they never named (Lillywhite Sessions was chosen for two reasons - producer Steve Lillywhite seems to be the one who said it was okay for these recordings to make it to the public; and this was the last time the band worked with Lillywhite on a studio recording).  When it was about time to release this album, the band agreed that these songs did not give off the atmosphere they were looking for, so they scrubbed this recording and created Everyday instead.  At some point after this release, fans found out about the scrubbed album and requested its release.  The band finally agreed to re-write 9 songs (excluding Sweet Up & Down, JTR, and Monkey Man) and add to them 2 new songs, to form Busted Stuff.  The fans soon realized that they were not getting the original versions of the 9 songs, and the original Lillywhite Sessions recordings leaked out across the internet.
 
Remember Two Things - What are the two things?
Apparently Dave wants us to remember these two things:  Love your mother and leave only footprints.

Davespeak
Dave Matthews and the other members of the band always have funny, interesting things to say between songs, and sometimes use this space to give quality intros or outros to songs.  Read a small collection of these here:  Davespeak, but NOTE:  There is plenty of bad language in this segment.