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Can you give me examples of songs with varying difficulty levels?

Easy: Tom Petty songs, both Ron and Howie. Not difficult, but groove hard.

I've had to learn a handful of Tom Petty tunes just in the past couple months for some local gigs, and I gotta admit, they are fun as all getout! Really easy to learn the changes -- tbh I suspect Petty only knew the bog standard cowboy chords -- but the magic happens in how tight/compelling the groove is, and how the multiple guitar parts get orchestrated around those simple chord changes.

Hard: Hello Jeff - Stanley Clarke. Very fast sig line dbl w/ Beck.
Fun but difficult double stop groove section under Beck's solo.

I'm pretty sure Jeff Beck is not doubling the fast signature line in "Hello Jeff". Rather, that's Stanley overdubbed, either on a Yamaha organ, or a piccolo bass through the Maestro Universal Synthesizer System.
btw, if anyone has a transcription of that lick, I would love to see it!
And yeah, the stuff Stanley is doing underneath Jeff's solo is off the hook! Total thrash power chord mayhem!
 
I cheated and looked at my bands playlist to come up with my three examples...

EASY:
- Most 12-bar blues songs. That's not denigrating blues as a genre - I play in a band that does a lot of them. But, unless the song has a distinctive bass line, and a lot do, you can often play relatively simple patterns of root, 5ths, flat 7ths, and octaves and sound very good.
- Pride and Joy by Stevie Ray Vaughan and Double Trouble, just to suggest one.

MEDIUM - This is a tough category because some of these will actually be easy for some players but difficult for others.
- American Girl by Tom Petty. I picked it because it's fun to play.

DIFFICULT
The door is WIDE open here. because there are a lot of songs that most players will admit are difficult. But here's an example that we play:
- Bodhisattva by Steely Dan. It came together quickly once we started rehearsing it, but we all put in a fair amount of time practicing at home before we even tried it in rehearsal. To be honest, we never actually played it straight through from start to finish in rehearsal before playing it live. The first time we ever played it all the way through was on a gig! Definitely NOT a smart thing to do but our singer REALLY wanted to get it in rotation and she wasn't taking no for an answer. FWIW, she only sings, she doesn't play an instrument. LOL. But, having played it for about two years, we play it pretty well now.
 
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I'm pretty sure Jeff Beck is not doubling the fast signature line in "Hello Jeff". Rather, that's Stanley overdubbed, either on a Yamaha organ, or a piccolo bass through the Maestro Universal Synthesizer System.

I agree that that fast line is, of course, Stanley plus George Duke on a synth doubling; but I think I hear Jeffs's crispy strat reinforcing the line as well in the guitar's lower register. Could be wrong, but it's not like Jeff didn't have the chop to play the line. ☮️

 
I agree that that fast line is, of course, Stanley plus George Duke on a synth doubling; but I think I hear Jeffs's crispy strat reinforcing the line as well in the guitar's lower register.

It's been decades since I poured over the liner notes on that album, but I'm pretty sure that George Duke doesn't play on "Hello Jeff". He's on "Silly Putty", "Journey To Love", and "Concerto For Jazz/Rock Orchestra".

"Hello Jeff" is just the trio of Beck, Clarke, and Lenny White on drums… but I'm fairly certain Clarke is also credited with playing organ on that tune.

In any case, I'd agree that the fast signature riff in that song is the primary qualifier for pushing it into the "Difficult" category.