There is a movie whose title I can't remember. It's fairly recent; I
think within the last 10 years (that's recent to me). It is the story
of a young man who is forced by circumstances to join a band of
grifters. As I remember it, they were grifters, but I can't really
tell you why I think so. Anyway, these people made their living
swindling homeowners out of the money paid to repave the owner's
driveways. They didn't repave; they just painted and when it rained
the paint washed off. Anyway, this young dude enters the group and
initially is repulsed by the group's method of making a living. He is
taken under the wing of an old member who teaches him the way the
group lives, works and plays. During the course of the movie the young
dude grows fond of the lifestyle, even as his mentor becomes alienated
from it. At the end the dude stays with the group and the mentor
leaves it. I am not very good at describing plots, but I'd like to see
this movie again. Awfully hard to do when I can't remember the title
or the names of anyone in it. You see my problem? Can anyone help?

It is good to see you again, Andy!

I believe you are thinking of "Traveller," an excellent 1997 film
starring Bill Paxton as an old grifter and Mark Wahlberg as his
apprentice.

Here is a synopsis of "Traveller" from Blockbuster's Web site:

"Actor Bill Paxton produced this unusual film about a clan of
Irish-American con artists practicing in the American South. They live
in a secluded compound and have their own time-honored customs. Pat
(Mark Wahlberg) is returning to the hideout for the funeral of his
father, who irked the clan by marrying an outsider. Because his mother
is not Irish, the compound's boss, Jack Costello (Luke Askew), tells
him that he's no longer welcome there. But Bokky, played by Paxton,
takes the younger man under his wing and teaches him the clan's trade.
Bokky specializes in cheating homeowners by charging them to apply
driveway or roof sealant, then leaving before they discover that it's
only black oil. He also buys and resells shoddy mobile homes. Pat soon
proves more nervy and creative than his boss. They try to scam a
bartender, Jean (Julianna Margulies), but Bokky falls in love with
her. Jean needs cash to pay for an operation for her hearing-impaired
daughter, so Bokky finally agrees to work for a cowboy con artist
named Double D (James Gammon), who has been trying to recruit him for
a big job in Nashville."

Blockbuster
http://www.blockbuster.com/bb/movie/details/0,7286,VID-V+++137680,00.html

You'll find more corroborative details in these reviews:

Flick Filosopher
http://www.flickfilosopher.com/flickfilos/archive/1q98/traveller.html

Reel Reviews
http://movie-reviews.colossus.net/movies/t/traveller.html

Film Vault
http://www.filmvault.com/filmvault/alibi/t/traveller_f.html

Movie Web
http://movieweb.com/movie/traveller/

This movie is readily available for rent and for sale, in both VHS and
DVD versions:

Amazon.com: Traveller DVD
http://www.amazon.com/exec/obidos/tg/detail/-/6305899592/qid=1034381141/sr=8-10/ref=sr_8_10/102-1777183-0301739?v=glance&n=507846

Amazon.com: Traveller VHS
http://www.amazon.com/exec/obidos/tg/stores/detail/-/video/157492446X/102-1777183-0301739

My search strategy:

Since I recognized the movie instantly from your description, the only
searching involved finding the plot summaries for you.

Google Web Search: "traveller" + "paxton"
://www.google.com/search?hl=en&ie=UTF-8&oe=UTF-8&q=traveller+paxton

While I am 99.9 percent certain that this is the film you remember, if
I am wrong in identifying your film, please request clarification, and
I will be more than glad to resume the search.

Best wishes,
pinkfreud

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Clarification of Answer by pinkfreud-ga on 11 Oct 2002 18:28 PDT

Thank you very much for the five-star rating!

If we researchers could rate customers, you would most certainly be
one of the five-star variety for your literate questions, friendly and
cooperative attitude, and quirky sense of humor.

Would you like to buy some asphalt? We just finished resurfacing a few
questions about driveways, and we can let you have the rest of this
load for a right fine price...

;-)

~pinkfreud

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Clarification of Answer by pinkfreud-ga on 11 Oct 2002 18:32 PDT

I notice that Half.com has several VHS copies of "Traveller." You can
buy it for as little as $3.94, shipped:

http://half.ebay.com/cat/buy/prod.cgi?cpid=2035081&domain_id=1877&meta_id=3

Ah, my old friend pinkfreud. How ever can I thank you for solving this
great mystery for me? I was prepared to spend a sleepless night,
valiantly searching the Internet but finding nothing. Now I can sleep
in peace. I have become quite fond of buying used copies of movies
because they are very inexpensive, and I will try to buy a used copy
of this one. Thank you again. But why does the conversation always
come around to beds and sheets and frustling thereunder?