One is kiddie music, which exists for my wife's iPhone (when I have the kids by myself, we listen to my music). The other is a Hold Steady playlist which has made several CDs for people. The only one I actually use is my "This month's music" playlist, onto which go my choices for the month's listening. It's between 4 and 6 albums, which get loaded onto the phone on the first of the month, and stay there.

History of Glam
Electronic 80s
Folk rock
German pop
French songs
Dutch hits
Psychedelia
UK psych
Northern Soul
Songs that remind me of school
Songs that were out just before Xmas but are not Xmas songs
Songs that remind me of moving to London
Autumn songs
British Blues
Reggae
various years from 1960 to 1990
Songs you don't hear on the radio anymore
One hit wonders of the 70s
Best of...all sorts of artists
Goth greats
Classic Rock
NWOBHM
New wave
Punk
Stadium Rock
Songs from films
TV themes
Midwest US
Various playlists I've burnt for friends
Krautrock
Australian pop
Instrumentals
US hits of the 80s
Novelty songs
Tropicalia

...and about a million Genius-generated playlists.

I'm rarely bored.

And many, many more

I like to let the iPod take control with Smart (i.e. random)playlists, so always include genre, the year of release and star rating for each track, and add comments like instrumental, live, acoustic etc., enabling me to get the iPod to come up with lists like:

5-Star 70's Rock
1 Hour of songs from [any year]
Pre-1960 Jazz instrumentals

... and so on. I also go though phases where I spend my commute listening to a different year each day for a few months. I find these all good ways of listening to the outer reaches of my collection, without putting myself entirely in the lap of the Shuffle Gods.

And I don't mean that as an insult to either of the two prior posts. Geeks get full potential of fun out of stuff by being organised and knowledgeable. I am neither.

So, like Metal Mickey says, if you can categorise stuff smart playlists suddenly become a lot easier and playback in shuffle avoids the horrible playlist rut where you're fooled into thinking your bored of your entire collection.

I have a few main smart playlists: stuff I've recently added; stuff that is newly released; stuff with a low playcount or that isn't rated (which forces a bit of organisation) and finally everything with 4 or 5 stars - good to fall back on. I use these to browse, rather than play through as a whole.

I've avoided Genius because I have this pet hate about machines doing all my thinking for me. (Twat.)

1. 5 star rated. Basically all of my favourite songs in one place. I'm very picky about what is in here & want it to be a back up for if i'm uninspired & can't decide what to listen to. I have a strict rule that if I fast forward past a song twice then its deleted from the list.

2. 5 of 5. Pick 5 bands you like & then 5 songs that you enjoy by said band. You end up with a 25 song playlist of tunes you should enjoy. I have 8 of these on my ipod & find them really good to listen to. If you are a loser (like me) then you can do a manchester one (fall, stone roses, james etc.) & then a liverpool one (la's, coral, teardrops etc.)

3. Recently added. Update it once a month & put in all new music from the previous 4 weeks. Is a good way to make sure that you listen to all new stuff & as long as its updated then it keeps fresh too. Although I can see you already do this with the train one you have.

I think that genius is crap - border line OCD is a much better tool for playlists!

I've never bothered rating my tracks. Not sure I could really start now...

I find it's a good idea to use the Genre and Comment fields wisely. For example, I put a code in the Comments field for each of the Soul Jazz tracks I like and let the Smart Playlist function take care of the work for me. I also like using the Genre field and date range, eg US Soul between 1960 and 1965.

I love making playlists and in doing so, trying to pin-point my own sub-genres and nuanced connections not always picked up on.

Apart from the 'best ofs', of my fave groups, here's a few of the sometimes clunky titles i have to identify a group of tracks.

Class Spirit of '92
Goodtime Saturday Night
21st Century Rn'R
All's well with the world (warm sounding records/production,...a lot of Hammond org on this)
Alt Pop Symphonies
Danceyish (danceable stuff tho not dance music as such)
Rebel Music (Marley/Clash/Cash/Redskins/Jam/LKJ, etc..)
Progressive Generations
Electro Sleaze (Peaches/NIN/Rev Co./PWEI etc...)
My late night tales
Best live tracks
Pop gets it's act together
The goth years
Killer harmonies
Lost gems and assorted curios
Dirty bass epics
3 song intros
Shambling, warm and loose
Summer at the stadium
Weird and wonderful covers

Why not listen to albums from beginning to end in the order in which they were sequenced?

Sorry, I sound like a fogey. And I love playlists and compilations. But you can have too much of a good thing, and I find it devalues the music after a while. Sometimes I find it better to listen to music in the old-school way.

There is a place for playlists.

Each week I have a playlist called "Week (#)", this week is the 26th since I started. I select 15 artists, and listen to as much of their stuff within that week as I can. Leads to discovering old things I'd forgotten I'd loved. I like it anyway.

have also got at the moment:

Skins - i.e. a list of music used in the TV program Skins
2010 / 2011 - a smart playlist from the last two years
Tracks - some of my favourite tracks
Wire - A selection of 16 songs by Wire
Summery tunes - Tunes that remind me of summer
Top 25 most played - for geeky insider knowledge
Purchased - self explanatory
Vurt - 20 tracks from a soundtrack to a film that doesn't exist of Jeff Noon's book Vurt - but if it did, these are the tracks I'd put in it

That's about it really - listening to 15 artists in a week takes up most of my listening time.

& persuade the artist to change the tracks on their albums. My current favourite is T.Rex Tanx. I tell Marc (who always listens to me) that he should open each side of vinyl with a single and include B sides that are better than album tracks, all recorded contemporaneously. So, his unco-ordinated, jumbled mix-bag becomes smooth, slick and perfectly formed:

Side One
20th Century Boy
Tenement Lady
Rapids
Mister Mister
Broken-hearted Blues
Electric Slim & The Factory Hen

Side Two
Children Of The Revolution
Jitterbug Love
Free Angel
The Street & Babe Shadow
Highway Knees
Left Hand Luke & The Beggar Boys

Tony Visconti couldn't have done better!!

I have loads of playlists, which are basically best ofs for artists, genres, etc, but one that I've done recently is an alternative Beatles one, which is compiled of a different version of all of their released tracks. I've only used versions of tracks from their 60's albums, singles and EPs and I have missed a few of the ropey ones out. There are live versions, alternative mixes, different takes, demos, etc and I've only used one different version of each track, but I might change a few versions as it takes my fancy. It's a great playlist and a fresh way to listen to very familiar songs. It's also nice to stick on when someone is around who isn't completely familiar with the official versions, because you keep getting puzzled looks from them when things don't sound quite right.

And I'm glad to have had this chance to explain it, because it took me hours, I was very proud of the idea and the finished product, but when I explained it to my darling FPO it was met with a "meh!".

I love playlists, and I certainly end up grouping together 'My [insert band here] Top 20' and similar.

But I notice the OP mentions using playlists to ensure they listen to a wide range of their music. This can take a bit of time, but I find that if I'm nagged by the feeling I'm somehow bypassing a lot of the tracks I've gathered over time, I make playlists up with themes that don't relate to the band or genre. (I think I have a lot of kinship with jonnyartist above over this.)

Just tracks that are under 3 minutes long.
Songs about London.
Best riffs or repetitive hooks.
Sultry female vocals.

And so on... it makes you sit in front of your iTunes (or whatever) and go rooting around. Great fun. Every now and again you'll hit on something that works so well you'll want to *cough*burn it for everyone, sorry, make all your friends aware of it.

1000s of soul and reggae, which are made up of lots of groups of two or three tracks by different artists, so playlisting them means I get to listen to just soul, with nothing else popping up. The same goes for my folk, and my electronics and punk and my mod and my 60s psych and garage and, and...

Then there are the playlists that are everything by a single artist who may have been in lots of different bands. New albums each get their own playlists. Sometimes I just create playlists of various tracks for the fun of it.

I don't think it's geeky. It's practical when there's so many tracks on the Pod.

60s, 70s, 80s, 90s, 00s - says it all, really.

Alternative Heroes - a bit of a mixture of Punk / New Wave with more esoteric stuff from the 60s.

Assorted Beatles ones - a Top 100 one, a 'Best of the Anthology', a 'Beatles solo' one and a covers one (Beatles covers by other people).

Electronic - assorted electronica, from the BBC Radiophonic Workshop to Goldfrapp.

Foreign Language - anything I've got that's sung in a foreign language. Be it covers (such as Seu George's Bowie stuff), obscurities, and the odd track which started out in a foreign language and became better known in English (Pino Donaggio's 'Io Che Non Vivo (Senza Te)', aka 'You Don't Have To Say You Love Me').

Made in Liverpool / Manchester / Wales - themed playlists based around the home cities / countries of the bands / artists concerned. Keep meaning to do a 'Made in Sheffield' one, as there's plenty of stuff I could use for that...

Movies - Songs and themes used in films

Girl's Names - basically, a big playlist of songs with girls' names in the title. Starts with 'Adia' by Sarah MacLachlan, ends with the Beatles' 'What's the New Mary Jane'.

Remixes - speaks for itself.

Stars & Stripes - stuff that references the USA, or various states therein.

Summer Sounds - not necessarily songs *about* summer, just things that put me in a summery mood.

The Odd Box - strange novelty / comedy records (i.e. Monty Python, Bonzos, Max Wall's cover of 'England's Glory', which has to be heard to be believed, etc.).

12" mixes - again, speaks for itself.

I've called it "Sad", ho hum......

Double post

'Hmm Nice' which is just anything melodic and relaxing, often used to lull me to sleep.

'Never Ending Playlist' no theme, just anything I like the sound of at the time, edited and re-arranged later to make some kind of sense.

...but my current favourites are

100 Songs - simply my favourite 100 songs, ever. If I add one, something else has to yield. Been on the go for five years now

Night Driving - quiet, contemplative. Paul Simon's "Hearts and Bones". That sort of thing

Music for Sunday Mornings - to calm the sore head. Charlie Hayden, Pat Metheny, Ali Farka Toure

Swingers! - Dino, Tony Bennett, excellent content added from a recent Word thread on instrumentals

Funky Sunshine - outdoor music for the sunshine

Anthems - an unholy mix of Aussie anthems (Paul Kelly, Hunna's, etc.) and Irish classics (Pogues etc.)

Type your name into Google.
Take the words from the description of the first search result.
Put these keywords into Spotify/iTunes and pick a song from the results.
A nice way of combining uniquely random with your own choices.

A Smart Playlist that plays songs with a play count of zero digs out the dark recesses of your iPod. It also should auto-refresh so that once it has played a song another one takes it's place.

specifically months - dunno why but i like to be able to look back and see what i was listening to - or intending to listen to at the time. June July and September get short shrift - no 09 or 10 purchases. Feb and March tend to be my most active months.

Basically they are the best three albums of each year going back to 1984 I used rocklist.net to look at the critics end of year favourites and then picked my own three favourites for each year