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I could go for my current favourite one in each category.
Strat- Ritchie Blackmore, probably Rainbow Rising era
Tele- I like Jerry Donahue, so probably his Telecasting album
Les Paul- Gary Moore for me. Lizzy, blues stuff, Blues for Greeny. Covers the main bases.
335? No preference really. Can't think of anything.
Gretsch- Billy Duffy. The Cult's Love is pretty much all White Falcon I think. Later albums are a mix of the WF and Lesters.
Strat - Wind Cries Mary, Jimi. Sultans of Swing, Dire Straits. Miserlou, Dick Dale. Over The Rainbow, Jeff Beck
Tele - Any song from Live at Sine, Jeff Buckley
Les Paul - I don't really know to be honest, I don't really listen to music that uses them? I can only think of Led Zeppelin, so I'll go for Dazed and Confused from Royal Albert Hall dvd.
ES 335 - I've no idea, sorry
Gretsch - was Black Hole Sun by Soundgarden on Cornells' Gretsch? Not the quintessential sound I suppose but hey ho. How about Psycho or Johnny Got A Boom Boom by Imelda May (guitarist Darrel Higham)
I'm not very good at this
Where the Streets Have No Name
Sultans of Swing
Gravity
Nowhere Man solo
Sweet Home Alabama
Tele
Communication Breakdown
Prove It All Night (preferably live around ‘78)
Paranoid Android
Tumbling Dice
American Girl
Les Paul
Sweet Child o Mine
Whole Lotta Love
All Right Now
Pretty Vacant
New Year’s Day (U2, preferably live around 2001)
The others are harder
Clapton, Layla
Hank, Apache
Beck, Where were You
Jimi, Purple Haze
Stevie, Couldn't stand the weather
Top 5 Tele
Danny Gatton, anything
Keef, Jumping Jack flash
John 5, Beat It
Guy from Radiohead, Creep
Jimmy Page, Whole Lotta Love
Top 5 Les Paul
Les Paul, How High the moon
Clapton, Stormy Monday
Jeff Beck, anything from Truth
Jimmy Page, Kashmir live
Buckethead, T.W.A.T .from the GnR album
Top 5 ES 335
BB, Thrill is gone
Clapton, Crossroads, Albert Hall
Larry Carlton, Steely Dan-Kid Charlemaigne
Dave Edmunds, Sabre Dance
Alvin Lee, Woodstock
Top 5 Gretsch
Malcolm Young, anything (everything)
Chet Atkins, not sure
Brian Setzer, Stray cat strut
Eddie Cochran, Summertime Blues
Billy from the Cult. Rain.
Where does EVH fit in??
the best tone, had to have a guitar built for it. ( 78 live show, supporting Sabbath )
Strat
Hey Joe - Hendrix
Slow Dancing - Mayer
Layla - Clapton
Where the Streets Have No Name - U2
Something to talk about - Bonnie Raitt
Tele
Cluster Pluck - Brad Paisley, James Burton, Vince Gill, Albert Lee (ok that’s a Musicman), John Jorgensen, Brent Mason, Redd Volkaert, Steve Wariner
Funky Mama - Danny Gatton
Caroline - Quo
Breakdown - Tom Petty Heartbreakers
Folsom Prison Blues - Johnny Cash
Les Paul
Alright Now - Free
Any Darkness from the first album
Any GnR from the first album
335
BB King - anything really
Room 335 - Larry Carlton
Mark Flanagan from Jools Holland’s Big Band has the one of the best live sounds I’ve heard.
Gretsch
Leave this town - Cousin Harley
Stray Cat Strut - Brian Setzer
Peter Gunn - Duane Eddy
Mayhem - Imelda May (Darrell Higham on guitar)
Chet - any
Hard to be Vaughan Brothers
Leaving Louisiana in broad daylight Rodney Crowell
Sweet Little Lisa Dave Edmunds
Luxury Liner Emmylou Harris
Les Paul
Ten Dollar Man ZZ Top
Brothers in Arms Dire Straits
Everything’s Broken Jason Isbell
ES335
Oh What a Thrill Rockpile
Please mr Postman The Carpenters
Child in Time Deep Purple
Gretsch
sitting in the Balcony Eddie Cochran
Act Naturally The Beatles
Perfect Fairground Attraction
Eddie Cochran and George Harrison would be first to spring to mind.
For Strat, it's basically Wind Cries Mary, Lenny by SRV and Cliffs of Dover. There's also Uli Jon Roth, but that's more just because I know he played a Strat, not because of "the tone".
For Tele, I always think of Prince, George Harrison, Tom Petty, and Zeppelin. But which songs exactly I'm not sure.
LP is just Guns n Roses.
335 is all over the map, isn't it? From Wes Montgomery to BB King to Dave Grohl?
Gretsch I think of anything from Chet Atkins to Elliott Smith to Chris Isaak to Jesus and Mary Chain.
But most importantly, tone is in the fingers.
Wicked game - Chris Isaak
Down to the waterline - Dire Straits
Trademark - Eric Johnson (cliffs had a solo on a 335 and this has all the classic strat tones in one song)
SRV - Little Wing
Slow Dancing in a Burning Room - Mayer
I'd also add Comfortably Numb but it sounds too good to be a strat, honestly!
And the "strat" sounds on Money and ABINW aren't even strats! Gilmour is a magician.