If there is any large category of iTunes offerings that are the most underrepresented by the iTunes Essentials system, it’s comedy.  Currently, I can easily locate exactly two iTunes essentials general comedy lists among the thousands of pro lists.  Contrast that with the mountain of comedy available on iTunes, and there is a gap to fill.

But rather than just point you at the best comedy tracks you can buy, I’d like to save you some money.  I’ve been a connoisseur of stand-up comedy for 25 years now, and have collected and listened-to hundreds of comedy albums.  There’s a difficult issue with buying comedy in iTunes: Most albums are divided up into 15 tracks or more.  At the usual price of $0.99 per track in iTunes, buying a couple of hours of comedy could be prohibitively expensive.  In some per-track collections, you’d run up a tab of over $50/hour to listen to your favorite comedians tell jokes.

But there is an obvious alternative, and that is to buy comedy in iTunes by the whole album.  To take the number one Essentials example below, purchasing all of Feelin’ Kinda Patton by the track would cost you a total of $27.72.  If you only really wanted to own half of the tracks on that album, it would run you $13.86.  But here’s the deal: You can buy the whole album right now for $7.99.

If you love comedy, purchasing whole albums in iTunes is the way to go.  But there are not yet any whole-album-save-you-money iTunes Essentials lists in the store.  I can’t even see a way to create a user-list that points at whole albums, rather than single tracks.

So let’s get on with the best comedy albums in iTunes, for the money:

The Basics

1. Feelin’ Kinda Patton by Patton Oswalt – At $7.99 for 28 tracks (runtime of 1.1 hour), Oswalt’s original brain freeze can’t be beat.
2. Retaliation by Dane Cook – Some people hate Dane for reasons I don’t grasp, but 29 tracks that deliver an incredible 1.7 hour runtime album – that went double platinum, by the way – for $13.99 is pretty good.
3. Monty Python Sings by Eric Idle and Monty Python – Six of their best songs are under a minute each, and all 25 tracks here are classic for $10.99.
4. Himself by Bill Cosby – Yes it’s only 7 tracks, only 46 minutes, but this is one of the greatest comedy albums ever, for only $6.63.
5. Holidays On Ice by David Sedaris – Who said comedy comes in stand-up clubs only?  Sedaris’ funniest book runs 4.3 hours long, for $16.95.
6. It’s Not Funny by David Cross – In my opinion, his best album.  For $7.99.
7. Strategic Grill Locations by Mitch Hedburg – The first stream of near-consciousness album from the late genius.  His next album is perhaps funnier, but any comedy lover wants more than 10 of these 21 tracks, so $9.99 is a good deal.

Next Steps

1. Shiny Happy Jihad by Joe Rogan – 1.1 hours of “I’m dying laughing” stuff from the man for $9.99.
2. Cheese And Crackers by Chris Rock – It’s a 19-track greatest hits package from one of the most successful standups of all time, for $9.99.
3. Incredibad by The Lonely Island – Saturday Night Live’s Digital Shorts-maker Andy Samburg’s greatest hits (so far) runs only 42 minutes, but is 19 tracks for only $7.99
4. A Night At The Met by Robin Williams – The only Williams comedy in the iTunes store, recorded at the peak of his work, is 16 tracks and 53 minutes for $9.99.
5. The Carnegie Hall Performance by Lewis Black – $9.99 gets you 1.4 hours of rants from the angriest sane man around.
6. Circle by Eddie Izzard – Because some tracks are up-priced, all 21 cost a total of $21.69 individually.  Get the whole album for $9.99.

Deep Cuts

1. Live At The DC Improv 4-5-08 by Eddie Gossling – A full set of the wildly underrated Gossling only puts you back $5.99.
2. It’s Bad For Ya by George Carlin – His last album, released posthumously, is $9.99 for 28 tracks that would cost you $27.72 individually.
3. You Can Win! by Maria Bamford – 21 tracks for $9.99. Every single one of them funny.
4. Greatest Comedy Hits by Eddie Murphy – If you’d buy 10 or more tracks of his individually, just get his 16 best  (plus a couple of others) for $9.99.
5. Comedy Central Presents: Stand Up – Each of these 21-minute tracks costs $1.99.  It’s cableTV-clean stuff you can pick and choose from.
6. 222 Live & Uncut by Patton Oswalt – Not an album, but two hour-long tracks for $0.99 each.  For sheer value, the best in iTunes.

Note: Comedy albums by the following artists are not available for purchase in iTunes: Richard Pryor, Richard Jeni, Roseanne Barr, Jim Norton or Vaughn Meader’s First Family (the highest selling comedy album of all time).

P.S. I love Katt Williams, but this is the worst value in all of comedy.  Cut that thing down by 80% at least!

I know what you’re thinking.

Of course iTunes has an Essentials listing for Aerosmith.

No, they don’t.

But, they’re the best selling American hard rock band of all time!  They have 150 tracks in iTunes!

Still, there is no iTunes Essentials listing for Aerosmith.  This is because only half of Aerosmith’s catalog is available in iTunes.  Aerosmith changed labels a couple of times, and were left with no relationship with the party that owns the rights to sell their first few albums.  Those are available on Amazon, but only as complete albums.  The iTunes Essentials team at Apple doesn’t want to classify Aerosmith’s best songs without the ability to promote half of them, or worse, by pointing to live versions of those songs that upset customers who think they’re getting the originals.  But that won’t stop me!

With over 150 million albums sold, 21 top forty hits and, 9 number one hits and four Grammys, Aerosmith was a shoe-in for the Rock And Roll Hall Of Fame, which inducted them in 2001.  Their success speaks for itself, and it baffles me as to why iTunes can’t just contain all their songs and promote them like I’m about to.  Essentials represents the starting point for collectors, as well as a concentration of the best for those who already have most everything.  This list covers 40 years of music:

The Basics

1. Dream On – Aerosmith’s signature song, the first single from their first, self-titled album.
2. Sweet Emotion – The breakthrough single from their third album, Toys In The Attic.
3. I Don’t Want To Miss A Thing – I’d like to, but can’t go on without highlighting Aerosmith’s greatest hit, from the 1998 Armageddon soundtrack.
4. Dude (Looks Like A Lady) – After a few years of ill-fortune, Aerosmith rocketed back with this single from Permanent Vacation.
5. Walk This Way – The memorable Toys In The Attic track goes here, but don’t forget the Run DMC mix, from their 1986 album Raising Hell.
6. Love In An Elevator – The complete package Aerosmith tune, from Pump, circa 1989.
7. Cryin’ – Big guitars, big horns, big bass, all that.  From the 1993 hitmaker album Get A Grip.
8. Come Together – The Beatles cover from the Sgt. Pepper movie was also featured on the Armageddon soundtrack, and is therefore available – barely – in iTunes.
9. Back In The Saddle – 1976 was the peak of ‘old Aerosmith’ success, and this track from Rocks would not literally come true until Aerosmith hooked up with Bruce Fairbain a decade later. (Live version)
10. Janie’s Got A Gun – Gritty social commentary from Pump, complete with nearly-R-rated David Fincher video.
11. Angel – The 80′s power ballad, and one of their most successful singles.  From Permanent Vacation.
12. Crazy – From Get A Grip, and most often remembered for music video starring Alicia Silverstone and Liv Tyler.
13. Hole In My Soul – Hugely sad song about loss and longing, from Nine Lives.
14. Jaded – Aerosmith pop for the 21st century, from Just Push Play.  Video starred Mila Kunis.
15. Same Old Song And Dance – The best track on Aerosmith’s 2nd album, 1974′s Get Your Wings. (Live version)

Next Steps

1. What It Takes – “There Goes My Old Girlfriend” starts this classic, from Pump.
2. Fever – A really great way to start something energetic, from  Get A Grip.
3. Deuces Are Wild – How often does the extra track on a greatest hits package turn out to be this good?  From Big Ones.
4. Rag Doll – A reminder of what a fantastic drummer Joey Kramer is, from Permanent Vacation.
5. Draw The Line – The title track from Aerosmith’s 1977 album.
6. Baby, Please Don’t Go – The oft-covered Big Joe Williams classic erupted from Aerosmith on 2004′s Honkin’ On Bobo.
7. Falling In Love (Is Hard On The Knees) – From Nine Lives, only their third single to sell over half-a-million copies.
8. Just Push Play – Aerosmith was pretty good at naming their albums after one of the best songs therein.
9. Young Lust – The lead track from Pump, well, rocks.
10. Big Ten Inch Record – Blues rock cover of a Bull Moose Jackson song, sexual innuendo intact, from Toys In The Attic.
11. Permanent Vacation – Was passed over as a potential single, but check out those guitars!
12. Pink – A not surprisingly heaping helping of sexual innuendo (and humor) from Nine Lives.

Deep Cuts

1. Livin’ On The Edge – Get A Grip‘s first single shot to #1 on the US Mainstream Rock chart.
2. Remember (Walking In The Sand) – Shangri-Las cover released as a standalone single in 1980.
3. Fly Away From Here – Beautiful ballad about moving on, from Just Push Play.
4. Kiss Your Past Good-bye – Sort of a natrual-pairing with the previous song, from Nine Lives.
5. Kings And Queens – Complicated number from Draw The Line.
6. The Other Side – Butt-kickin’ rock, horns and rhymes from Pump.
7. I’m Down – On Permanent Vacation, Aerosmith didn’t yet know how up they were.
8. Blind Man – A tall tale of wonder from Big Ones.
9. What Kind Of Love Are You On – That greatest hit from the Armageddon soundtrack was so huge that it had coattails.  This song was on them.
10. Angel’s Eye – Surprisingly impossible-to-find single from the Charlie’s Angels soundtrack.  Currently excluded from iTunes.
11. Taste Of India – Tribute to the 2nd largest country on the planet, from Nine Lives.
12. Amazing – The song this list was destined to end on.  The last track on Get A Grip.

It’s amazing – with the blink of an eye, you finally see the light.  It’s amazing – when the moment arrives that you know you’ll be all right.  It’s amazing, and I’m saying a prayer for the desperate hearts tonight.

Good night!

It’s a link to an entire area feature of iTunes that helps you discover an artist or sound or style of music.  It’s also a unique free service that has caused many to practically depend on it.  Simply put, if there is an artist that you think you like, but you don’t really know which of their songs to buy, iTunes Essentials gives you an introduction to that artist that goes right to the best songs by that artist.  The iTunes Essentials editor divides up that artist’s most endearing songs into layers, with the first being called “The Basics”, the second is labeled “Next Steps” and then a third level of songs, “Deep Cuts”.  Each layer contains 12-15 songs, which is perfect for burning to a CD if you still use such things.

For artists that have fewer than, say, 25 songs that the iTunes Essentials editor is willing to recommend strongly, she drops one of the levels.  For example, 3 Doors Down in iTunes Essentials only has “The Basics” and “Next Steps”.

What occurred to me about iTunes Essentials, as I fell in love with it over the past few months, is that it can’t just be an automatic thing.  iTunes can’t just rank an artist’s songs based on their popularity in iTunes and then divvy them up like this.  Rather, an actual person who knows the catalog has to devote time to determining which songs to present.  There are just too many factors to consider.  You’ve got people from all over the world who come along and think to themselves:

I have an idea that I might really like this artist, but I don’t know his catalog, and I don’t know which of his songs to collect first.

If iTunes just left that up to everyone else, they would not get the best results.But here’s the problem – a world of people are accessing iTunes right now, looking for Essentials lists for artists that have a lot of really good music in iTunes, and finding nothing.  I’ve decided to help out.  Perhaps you came to this blog post looking specifically for this.  If so, I hope you like my suggestions.  Perhaps iTunes will make an Essentials list of their own for this artist in the future.  If so, it will be fun to compare my list to theirs.

Toto had a 31 year run, during which they released 17 albums, and sold more than 30 million records.  They ostensibly broke up in 2008, but leave behind a legacy of worldwide success that few artists can claim.  It is inexplicable that iTunes does not yet have a Toto Essentials page.

The Basics

1. Africa – If you only know one Toto song, it’s this one.  So over-played as to be considered trite.
2. Rosanna – Along with Africa, made the album Toto IV a six-Grammy winner.
3. Hold The Line – Toto’s first big single from their first, eponymous album.
4. I’ll Be Over You – From Toto’s sixth album, Fahrenheit. Reached #11 in the US.
5. I Won’t Hold You Back – The third top-ten single from Toto IV.
6. 99 – The main single from Hydra, Toto’s second album.  Inspired by Get Smart.
7. Pamela – From The Seventh One, one of the best of Toto’s many songs about girl names.  Features vocal by Joseph Williams, son of legendary composer John.
8. Girl Goodbye – From their first album, a rocking track that should have been released as a single.
9. Without Your Love – The other single from Fahrenheit, with a funky bass-line that just don’t stop.
10. I Will Remember You – The first single from Toto’s 1995 return to glory, Tambu.
11. (I Can’t) Stop Loving You – From The Seventh One.  Joseph Williams had some impressive chops.
12. Waiting For Your Love – This list is destined to contain most of Toto IV.
13. The Other End Of Time – One of the saddest songs ever written, with blistering lyrics on a David Paich piano from Tambu.
14. Stranger In Town – The only single from Isolation, their fifth album, which otherwise was a flop compared with its predecessor.

Next Steps

1. Til The End - The first track on Fahrenheit, clocking in at a respectable 5:28.
2. Afraid Of Love – Hard rocker from Toto IV.
3. Lovers In The Night – The next cut from Toto IV.  Trust me, this song has to follow Afraid Of Love.
4. Anna – Every other good Toto song was a girl’s name.  This girl was on The Seventh One.
5. Child’s Anthem – The very first song on Toto’s first album.  A short but sweet instrumental.
6. I’ll Supply The Love - Goes together with Child’s Anthem like a one-two punch.
7. If You Belong To Me – From Tambu, a love song about loss and guilt.
8. St. George And The Dragon – From Hydra, a part of the fantasy story that made this album near-prog.
9. Straight For The Heart – Boy meets girl, sparks fly. From The Seventh One.
10. Make Believe – Piano rock from Toto IV.
11. Could This Be Love – Question answered, on Fahrenheit.
12. Just Can’t Get To You – Frustration and longing, from Tambu.
13. Out Of Love – A waltz love song that was included as a new release on Toto’s first major hits compilation, Past To Present.
14. A Secret Love – A love song that almost whispers its question in your ear, from Hydra.

Deep Cuts

1. Rockmaker – From Toto, with hopes for a big single that didn’t quite pan out.
2. Goin’ Home – Recorded in 1989, but didn’t see the light of day until Toto XX in 1997.
3. Mushanga – Difficult, challenging track from The Seventh One about seeing a starving girl in Cape Town.
4. Dave’s Gone Skiing – Instant live hit, and memorable instrumental from Tambu.
5. While My Guitar Gently Weeps - The only cover here, from Through The Looking Glass.
6. Georgy Porgy – A finger-snapping little bass-line ditty from Toto’s first album.
7. Kingdom Of Desire – Specifically from Absolutely Live, far superior to the studio version.
8. English Eyes – The only song to highlight from Turn Back.
9. We Made It – From Toto IV, we made it before, I know that we can make it again.
10. The Road Goes On – A sign-off classic, from Tambu.
11. A Thousand Years – From The Seventh One, about how some things last.
12. Don’t Stop Me Now – Yes, that’s Miles Davis, and pretty much only Miles Davis.  Yes, that Miles Davis.  From Fahrenheit.
13. Bottom Of Your Soul - Toto’s last single, from Falling In Between.  Deserves the last deep cut spot.

Questions?  Comments?  Suggestions?  Complaints?  Feel free to leave them here!