A brother in Christ recently purchased his very first iPod and asked me to recommend podcasts. Fortunately, there are a number of great (and free!) Christian podcasts that are available and that I listen to on a regular, if not a weekly, basis.
Check out (by typing into the iTunes store search engine):
1) Mars Hill Church. Not to be confused with Mars Hill Bible Church (where Rob Bell preaches and is drifting farther left every week), this is where Mark Driscoll preaches. Mark was immortalized by Donald Miller in his book "Blue Like Jazz" as the "Cussing Pastor." Mark, however, doesn't drop any F-bombs or anything during his weekly sermons that are uploaded on-line (sorry to dissapoint). Mark is, in my opinion, the best "emerging" preacher out there in that he is, in his own words, "theologically conservative but culturally liberal."
2) Relevant Magazine. A weekly podcast featuring the editorial staff of Relevant Magazine (which you should subscribe to!) pontificating on news of the weird, pop culture, etc. A lot of fun. I never miss it.
3) "Dirty Little Secrets" by the XXX Church. A weekly 1/2 hour podcast featuring Craig Gross of the XXX Church which is a ministry geared to converting those in the porn industry and ministering to those addicted to pornography. A great ministry that is shining Christ's light into the darkness. If you are a dude then go to their website (google it) and get their software which blocks porn on your computer. No reason to even have the temptation in your house. Also consider buying Bibles for them to hand out to those at porn conventions or buying their shirts which supports their ministry and feature slogans like "porn sucks" and "Christian Men Don't Masturbate." But be warned, these guys work for Christ in the gutter and their language reflects it.
4) Wallbuilders. A daily podcast featuring David Barton and Rick Green and focusing on a wide range of public policy issues from a theological and historical point-of-view. Fantastic stuff!
5) Desiring God. John Piper's weekly sermons and Piper is the MAN. 'nuff said!
If you are a theology geek like me then be sure to check out podcasts from Dallas Theological Seminary and Covenant Theological Seminary. Both feature deep theological discussions and/or Bible classes online. Great for a nerd like me.
There are many others that might interest you. Just click on "Podcasts" then "Religion & Spirituality" and then "Christianity" for a list of the top 20 Christian podcasts. You'll find some great stuff!
May God bless your downloads!
Be sure to check 'em out and tell them that Pastor Matt sent ya'.