Best canidates for lifesteal: AA based ranged champions, and bruisers. Either you are an ADC who deals high amounts of sustained damage with occasional massive bursts (IE Crits), or you have to be tanky so that the health replenishment goes farther. The reason why you wouldn't run lifesteal on Volibear is that he scales much better as a tank, and so turning him into effectively a melee carry with those items would hurt him more than help.
Any ranged carry obviously works well with life steal because they are safer when it comes to auto attacking.
Most melee characters that benefit from lifesteal have an innate and consistent healing system already and they combine them for even more massive healing, often coupled with a
Spirit Visage. These champions are also often duelists and don't really seek to team fight, but rather splitpush and fight 1-2 people at a time.
Examples:
Aatrox
Lee Sin
Nasus (top lane only)
Rengar
Trundle
Tryndamere
Udyr
Xin Zhao
Warwick
Your example given is
Volibear, who has an inconsistent heal, scales better with AS/Health than damage (Which most lifesteal items give). I could see
Blade of the Ruined King being good on him, but not the other lifesteal items.
Most melee characters that benefit from lifesteal have an innate and consistent healing system already and they combine them for even more massive healing, often coupled with a

Examples:









Your example given is


jamosmith wrote:
I'm talking specifically about building stuff like:





I'm pretty sure Tryndamere is literally the only champion who could get away with that build. Mayyyyyybe Aatrox but I haven't played him to see how tanky he needs to be.
Champions that use lifesteal well are pretty much the ones that build 1-2 (or more) AD items. Some champions (such as Volibear) have kits that are better suited to defensive itemizations. You'd probably do better with stuff like





Thanks to Hoppermh for the sig!
PsiGuard wrote:
I'm pretty sure Tryndamere is literally the only champion who could get away with that build. Mayyyyyybe Aatrox but I haven't played him to see how tanky he needs to be.
He would never survive a team fight like

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I'm guessing a strong auto attack, but where are the numbers?
I'm talking specifically about building stuff like: