Which headphone do I get? Musical preferences are rock and jazz, particularly Dave Matthews Band.

Do you need closed back, or is open backed okay? Can you try either on first? 
 
Grado's particularly can be uncomfortable. I can wear mine for a few hours, but then I really need a break.
 
If you can stand the comfort and do not need closed backed, the sr 225 are great. I have not tried the Sennheisers, but I have heard great things about them.

harath said:

  Do you need closed back, or is open backed okay? Can you try either on first? 
 
Grado's particularly can be uncomfortable. I can wear mine for a few hours, but then I really need a break.
 
If you can stand the comfort and do not need closed backed, the sr 225 are great. I have not tried the Sennheisers, but I have heard great things about them.

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Both open and closed back should be fine.
 
But yes, comfort can be an issue.

Both are good at what they do. 
 
Both are on ear and comfort, especially for longer sessions can be an issue--at least for some. Headphone comfort is a very individual thing.  Sizing and sensitivities are unique to each person.  We can point you to headphones that are generally considered to be comfortable and mention others that have garnered complaints for being uncomfortable.  However, the only way to know for sure is to wear them yourself for a time equivalent to your longest listening session.  I personally find the Grado to be the more comfortable of the two, but your mileage may vary widely.
 
The Senn has more bass, but I prefer the overall sound of the open Grado.  The forward Grado is a master of rock and electric blues.  They are good with jazz, especially with smaller to smallish medium ensembles.  The Senns are a solid all arrounder, but being closed limits their sound stage--even when compared to "sitting on the stage with the band" Grado presentation.