1. Han Solo, the Very Emotional Dad
After his defining moment -- leading an army of teddy bears against a battalion of fascists -- Han Solo's life in the original Star Wars expanded universe took all the turns you'd expect. He kept working with the Rebel Alliance, which quickly morphed into the New Republic, and eventually the Galactic Federation of Free Alliances.
Even as he married one Leia Organa, becoming the father of three in the process, Solo got up to all kinds of free-wheeling murder-y antics. Notably, he managed to kill the last, Force-possessed clone of Emperor Palpatine. Between these missions, and with Leia busy running an entire galaxy, Han was also (happily) left with the role of stay-at-home dad over the pair's children: Jacen, Jaina, and Anakin Solo.
This arrangement worked out just fine for all involved until a minor scuffle known as the Yuuzhan Vong War, a conflict which left something like 365 trillion people dead.
Among those casualties was one hairy mechanic called Chewbacca. Han's best friend and confidant (you can always trust your secrets with someone who only communicates in growls) was killed saving young Anakin. Han, showing little appreciation for heroic self-sacrifice, blamed his son for this, sending him on a spiral of bad parenting and life decisions that would come back to bite him throughout his remaining years.
Said decisions include: siding with his home world of Corellia against his family and friends in a galactic civil war, leaving his other son, Jacen, to become a Sith Lord, and painting the Millennium Falcon matte-black in a terribly gauche display of mourning no matter how far away your galaxy is.
Anakin bit the dust shortly after Uncle Chewie, and well before Jaina was forced to kill her then-evil brother Jacen. Despite all the tragedy, however, Han and Leia managed to fill the void with their grandchild (Jacen's daughter). Together they toddled off more-or-less happily ever after up to the death of the expanded fiction.
2. Luke Skywalker, the Really Unlucky One
You'd think that one of the last surviving Jedi's top priorities after the death of Emperor Palpatine would be to revive the pseudo-religious order, thereby keeping his kind from extinction. You'd be right, of course, and that's exactly what Luke Skywalker intended after his touching reunion with dead friends and relatives.
Unfortunately, the universe doesn't give a damn about what we want -- apparently even if what we want is to worship the physical will of the universe. Before he could kick off a new Jedi drum circle, Luke was embroiled in the greatest battle of them all: love.
Well, love and a few other, literal battles. Battles like the one against Grand Admiral Thrawn, heir to what was left of the Galactic Empire in the wake of Palpatine's death. It was around this time, however, that he ran into Mara Jade -- the late Emperor's assassin/secret agent/just kind of a jerk.
Jade (justifiably) blamed Luke for ruining the life she'd worked hard to achieve. Not to mention that her last order from her dead emperor was to kill the guy anyway, so it worked out.
What didn't work out was how she predictably fell in love with Luke during their many encounters with one another. This came to a head when together the two fought Thrawn's requisite mad scientist, Joruus C'baoth. Joruus had scooped up Luke's severed hand -- the one he lost in The Empire Strikes Back -- and grown it into the clone Luuke Skywalker. Despite his lineage, Luuke lasted all of 10 seconds against the lovebirds-to-be, and Mara finally got to kill her final target. Sort of.
The pair remained cuddly as Luke briefly fell to the dark side, finally established that New Jedi Order he'd been procrastinating on, and had themselves a kid named Ben.
Their time together was frustratingly brief, however. Luke's own nephew, Jacen Solo, killed Mara and left him a widower. Shortly after that he was exiled from Coruscant, and in the process the seat of the Jedi Order's power. Even that wasn't enough to stop him from continuing to do the right thing, however. As a Force ghost Luke would go on helping his descendant Cade Skywalker decades after his own death.