I think all of these are good to great, worth seeing anyway (in no particular order)...
Detour (1945 - Edward G. Ulmer)
Easy Rider (1969 - Dennis Hopper)
Lost in America (1985 - Albert Brooks)
Paris, Texas (1984 - Wim Wenders)
Scarecrow (1973 - Jerry Schatzberg)
Paper Moon (1973 - Peter Bogdanovich)
The Sugarland Express (1974 - Steven Spielberg)
North by Northwest (1959 - Alfred Hitchcock)
A Perfect World (1993 - Clint Eastwood)
The Passenger (1975 - Michelangelo Antonioni)
Rain Man (1988 - Barry Levinson)
Starman (1984 - John Carpenter)
Fandango (1985 - Kevin Reynolds)
Little Miss Sunshine (2006 - Dayton & Faris)
Kalifornia (1993 - Dominic Sena)
Badlands (1973 - Terry Malick)
Last Orders (2001 - Fred Schepisi)
Midnight Run (1988 - Martin Brest)
Week-End (1967 - Jean-Luc Godard)
Transamerica (2005 - Duncan Tucker)
Two for the Road (1967 - Stanley Donan)
Five Easy Pieces (1970 - Bob Rafelson)
The Last Detail (1973 - Hal Ashby)
Broken Flowers (2005 - Jim Jarmusch)
Stranger Than Paradise (1984 - Jim Jarmusch)
Nurse Betty (2000 - Niel LaBute)
Leaving Normal (1992 - Ed Zwick)
Highway 61 (1991 - Bruce MacDonald)
Hawks (1988 - Robert Ellis Miller)
Payday (1972 - Daryl Duke)
Honkytonk Man (1982 - Clint Eastwood)
Bound for Glory (1976 - Hal Ashby)
Thieves Like Us (1974 - Robert Altman)
Box of Moonlight (1996 - Tom DiCillo)
The Sure Thing (1985 - Rob Reiner)
Thelma & Louise (1991 - Ridley Scott)
The Mexican (2001 - Gore Verbinski)
Wild at Heart (1990 - David Lynch)
The Hitcher (1986 - Robert Harmon)
The Hitch-Hiker (1953 - Ida Lupino)
Freeway (1996 - Matthew Bright)
RoadGames (1981 - Richard Franklin)
Six-String Samurai (1998 - Lance Mungia)
One False Move (1992 - Carl Franklin)
Sullivan's Travels (1941 - Preston Sturges)
The Rain People (1969 - Francis Ford Coppola)
Something Wild (1986 - Jonathan Demme)
Vanishing Point (1971 - Richard C. Sarafian)
Two-Lane Blacktop (1971 - Monte Hellman)
Electra Glide in Blue (1973 - James William Guercio)
Wages of Fear (1953 - Henri-Georges Clouzot)
The Electric Horseman (1979 - Sydney Pollack)
The Straight Story (1999 - David Lynch)
It Happened One Night (1934 - Frank Capra)
My Own Private Idaho (1991 - Gus Van Sant)
Pieces of April (2003 - Peter Hedges)
Running on Empty (1988 - Sidney Lumet)
The Opposite of Sex (1998 - Don Roos)
The Music of Chance (1993 - Philip Haas)
In This World (2002 - Michael Winterbottom)
Gas Food Lodging (1992 - Allison Anders)
Y Tu Mama Tambien (2001 - Alfonso Cuaron)
About Schmidt (2002 - Alexander Payne)
O Brother, Where Art Thou? (2000 - Joel & Ethan Coen)
Planes, Trains & Automobiles (1987 - John Hughes)
Fear & Loathing in Las Vegas (1998 - Terry Gilliam)
Bring Me the Head of Alfredo Garcia (1974 - Sam Peckinpah)
Alice Doesn't Live Here Anymore (1974 - Martin Scorsese)
The Adventures of Priscilla, Queen of the Desert (1994 - Stephan Elliott)
National Lampoon's Vacation (1983 - Harold Ramis)
Smokey & the Bandit (1977 - Hal Needham)
And picking out five of my very favorites from my list...
Paris, Texas (1984)
Wim Wenders' beautiful movie about the purgatories we put ourselves in and the possibilty of redemption for those in our wake. Harry Dean Stanton is so quietly perfect as the sad, dusty wanderer. The payoff scene between him and Nastassja Kinski in the cathouse is one of my all-time favorite moments in cinema.
Lost in America (1985)
Albert Brooks' masterpiece subversion of the American Dream, gah-damn hysterical too. Turning their backs on the fast-track of suburbia and hitting the road to find themselves, our married couple learns even dropping out isn't as easy as it used to be. "Have you seen
Easy Rider? Well you should, it's historic." And remember, avoid Vegas completely.
The Hitcher (1986)
The best coming-of-age, action-filled, horror thriller, seemingly-supernatural psychopath on the rampage road movie ever made. Bar none. And this may be
the definitive Rutger Hauer role (yes, even more than Roy Batty). Kids, this is why your momma always told you never to pick up hitch-hikers. Lots of fun to watch, though. A stylish nightmare on a desert road. And the first person to mention the re-make I chain between two trucks and let out the clutch.
The Passenger (1975)
My favorite Antonioni film and my favorite Nicholson performance, a perfect and hauntingly beautiful Existential statement. A still, dusty hallucinatory journey to the center of identity and self. There, but not back again.
Paper Moon (1973)
A subtle, beautifully-crafted character piece, set in the dust bowl of The Depression, following a low-rent con man and his unlikely companion who turns out to be a natural. Flawless performances by all, absolutely charming, filmed in beautiful black and white.
All different, all wonderful.